ライフサイエンスコーパス: pentacyclic

1 ominated phthalide to generate a substituted pentacyclic 12H-5,11a-diazadibenzo[b,h]fluoren-11-one in

2 we show that replacing the anthracenes with pentacyclic 5,7,12,14-tetrahydro-5,7,12,14-tetraoxapenta

3 The occurrence of triterpene pentacyclic acids in plants is extensive, but little is

4 The pentacyclic acridinium salt RHPS4 displays anti-tumour p

5 A synthesis route to the pentacyclic alkaloid (-)-gilbertine, which features a cy

6 The pentacyclic alkaloid calothrixin B (1) has been synthesi

7 The first synthesis of a pentacyclic ambiguine (ambiguine P) is reported.

8 guine G, the first member of the chlorinated pentacyclic ambiguines to yield to chemical synthesis.

9 -membered ring that is characteristic of the pentacyclic ambiguines, as well as the use of an amide-d

10 be applicable to the synthesis of the other pentacyclic ambiguines.

11 Photophysical studies reveal that these pentacyclic ammonium salts exhibit strong emission in th

12 sults in the formation of highly fluorescent pentacyclic ammonium salts in excellent yields.

13 The convergent synthesis of two pentacyclic analogues of the polyether monensin A is des

14 ial lanosterol synthase enabled synthesis of pentacyclic arborinols in addition to tetracyclic sterol

15 system, 4 bears an uncommon 9/5/6/10/3-fused pentacyclic architecture, and 8 is a dimer bridged by an

16 key reactions used in the synthesis of this pentacyclic Aspidosperma alkaloid were a deracemizing im

17 nderlying functional interconversion between pentacyclic beta-amyrin synthase (CqbAS1) and B,C-ring-o

18 pe cross-coupling to construct the tetra- or pentacyclic bridged framework.

19 lides leading to substituted tetracyclic and pentacyclic bridgehead N-heterocycles, wherein iodonium

20 tructures via oxidation of the corresponding pentacyclic C19-iminium ions.

21 Two series of pentacyclic carbazolones, 22 and 23, have been synthesiz

22 to-tail heterodimers with a unique 5/6/6/6/5 pentacyclic carbon skeleton, designated as bipentaromyci

23 2 possesses an unprecedented 6/6/5/6/7-fused pentacyclic carbon skeleton.

24 atalyzed cleavage of the ester side chain of pentacyclic cinnamyl ester 15.

25 enzothiophene, the anti and syn isomers of a pentacyclic compound consisting of alternating thiophene

26 With an overall yield of 6.4%, this pentacyclic compound has been synthesized by utilizing o

27 and heteroaromatic pi-bonds to provide novel pentacyclic compounds in good yield and in a stereocontr

28 ane-containing PIAs into a distinct class of pentacyclic compounds remains unknown.

29 Hopanoids are triterpenoic, pentacyclic compounds that are structurally similar to s

30 novel molecular scaffold, bearing 6-6-6-5-6 pentacyclic core is described that proceeds via (i) pipe

31 A concise preparation of the prochiral pentacyclic core of (+)-salvileucalin B is presented.

32 establish the remaining stereocenters in the pentacyclic core of (-)-citrinadin A.

33 The synthesis of the pentacyclic core of alkaloid nakadomarin A is described.

34 ype reaction for the construction of the key pentacyclic core of both targets, bearing either the nat

35 The pentacyclic core of rutaecarpine alkaloid analogues is e

36 establish the remaining stereocenters in the pentacyclic core of the citrinadins.

37 rboxamide forms the D ring and completes the pentacyclic core of the morphinans.

38 tall the eight-membered endoperoxide and the pentacyclic core of the natural product, respectively.

39 The route to the pentacyclic core relies on a new regioselective alkenyla

40 After C21-oxygenation, the pentacyclic core was accessed by electrophilic C19-amide

41 opening sequence enabled construction of the pentacyclic core.

42 chloride to generate the generic celastroid pentacyclic core.

43 single-pot operation provides access to the pentacyclic coumarin-fused pyrrolo-dihydroisoquinoline c

44 deuterium atoms can be incorporated into the pentacyclic crambescidin core.

45 cloeucalenol cycloisomerase (EC ) to convert pentacyclic cyclopropyl sterols to conventional tetracyc

46 Chemoselective N9-oxidation of a pentacyclic deoxoapodine precursor enabled the synthesis

47 rrolo[2,1- a]isoquinoline and coumarin-fused pentacyclic derivatives were synthesized via base-mediat

48 d extended to mixed linear-angular annulated pentacyclic dibenzo[a,h]fluoren-13-one.

49 e have developed a number of fused tetra- or pentacyclic dihydrodiazepinoindolone derivatives with ex

50 de with 2,3-dichloronaphthoquinone to give a pentacyclic dinaphthofuran directly, followed by convers

51 A new class of pentacyclic diquinoid compounds has been synthesized wit

52 ize the cyclic structures of many tetra- and pentacyclic diterpenes, including ent-beyerene, ent-kaur

53 divergent total synthesis of two symmetrical pentacyclic dithiodiketopiperazines, (-)-epicoccin G and

54 uction of a late-stage protecting-group-free pentacyclic enol triflate coupling partner, from which a

55 The rapid synthesis of this key pentacyclic enol triflate was achieved by a highly conve

56 e (1) at the 2,3- and 3,4-positions gave two pentacyclic enones (7 and 10) that contain A/B-cis-fused

57 (d) base-promoted skeletal rearrangement of pentacyclic equatorial alcohol 82 to form the oxacyclic

58 mpounds 8 and 32, each of which embodies the pentacyclic framework and much of the functionality asso

59 c aniline onto the oxindole moiety to form a pentacyclic framework containing the southern aminal, a

60 The challenging pentacyclic framework of the natural product was assembl

61 s of an indole core to rapidly construct the pentacyclic framework of the natural product.

62 annelated ring size led to formation of the pentacyclic framework with complete diastereoselectivity

63 With access to a C-3 epi-pentacyclic framework, 3-epi-jorumycin (32) and 3-epi-re

64 inocarbene promotes the planarization of the pentacyclic framework, resulting in the synthetic realiz

65 aloid bearing a 2-acylindoline moiety in its pentacyclic framework.

66 featuring a synthetically challenging caged pentacyclic framework.

67 indoline and construct the natural product's pentacyclic framework.

68 of chiral polycyclic molecules (tricyclic to pentacyclic) from achiral polyene precursors by enantios

69 nt chemoselective reduction of the resulting pentacyclic furfuryl ketal, furnishing a keystone interm

70 (HFIP) and visible light to synthesize novel pentacyclic-fused aminothiazoles and amino-selenazoles.

71 radiation, which results in the formation of pentacyclic-fused thiazoles or selenazoles.

72 pening of the spirocyclic ether rings of the pentacyclic guanidinium moiety.

73 rom the endo-oriented nitrile substituent of pentacyclic Heck product 18 were unsuccessful.

74 hexenyl radical derived from 48 produces the pentacyclic heterocycle 50 by either a direct 6-endo tri

75 Diels-Alder reaction to rapidly assemble the pentacyclic heteroyohimboid derivative 8 from the readil

76 etracyclic carbon skeleton and the 6,6,6,6,5-pentacyclic hopanoids.

77 nochemical reactivity of the highly strained pentacyclic hydrocarbon cubane.

78 nally enhanced, higher order fluorenols like pentacyclic indeno[1,2-b]fluorene-6,12-diols and further

79 eloped for the enantioselective synthesis of pentacyclic indole derivatives with the yohimbane skelet

80 a nanomolar inhibitor of Ca2+-ATPase, has a pentacyclic indole tetramic acid scaffold that arises fr

81 lar inhibitor of Ca(2+)-ATPase with a unique pentacyclic indole tetramic acid scaffold, is assembled

82 BS resulted in the formation of the required pentacyclic indoline framework of the target alkaloid.

83 Alstonine and serpentine are pentacyclic indoloquinolizidine alkaloids (referred to a

84 A prototype pentacyclic inhibitor 32 (AKI-001) derived from two earl

85 (+)-paucidactine D (4) is detailed from the pentacyclic intermediate 13.

86 (-)-deoxoapodine are detailed from a common pentacyclic intermediate 15, enlisting the late-stage fo

87 neram (11) were also achieved via the common pentacyclic intermediate 16.

88 reochemically rich and highly functionalized pentacyclic intermediate 8 as a single diastereomer in o

89 c oxygenases to further modify the 6/5/5/6/6 pentacyclic intermediate en route to the complete 21R-ci

90 chanism involves the formation of a putative pentacyclic intermediate formed by a 1,3 dipolar cyclo-a

91 e synthesis, in which the structure of a key pentacyclic intermediate is corroborated by X-ray crysta

92 An 8-step synthesis of a known pentacyclic intermediate toward the natural product pleu

93 This pentacyclic intermediate was subsequently transformed to

94 yclization precursor, leading to a versatile pentacyclic intermediate.

95 ltimate C21 functionalized Aspidosperma-like pentacyclic intermediate.

96 efficient aza-Cope/Mannich reaction to give pentacyclic ketone rac-44.

97 fragmentation products were synthesized from pentacyclic ketones 3 and 4 via Baeyer-Villiger oxidatio

98 4 and, after oxidation of the olefin 16, the pentacyclic lactam 17 with a brigehead double bond.

99 n Ullmann-type lactone ring closure into the pentacyclic lamellarin skeleton.

100 ibe how a biomimetic synthesis of bruceol, a pentacyclic meroterpenoid, led to the anticipation, isol

101 tep total synthesis of arborisidine, a caged pentacyclic monoterpene indole alkaloid, has been accomp

102 exceptionally efficient way to construct the pentacyclic nucleus of the Daphniphyllum alkaloids.

103 iously in the 3-, 6-, or 10-positions of the pentacyclic nucleus.

104 from the angular methyl configuration of the pentacyclic or 6-6-6-6 tetracyclic product.

105 of 6,12-diboraindeno[1,2-b]fluorene (DBIF)-a pentacyclic pai-system with diboron incorporation-are re

106 The first total synthesis of the pentacyclic phenylnaphthacenoid type II polyketide antib

107 directly converted at lambda = 366 nm into a pentacyclic product (47% yield) by a three-photon cascad

108 in the presence of silver phosphate to form pentacyclic product 69 having the unnatural configuratio

109 this material to SnCl4 then gave the desired pentacyclic product, which was identical to that previou

110 The latter reaction sequence generated pentacyclic products with a central [1,5]dioxocane ring.

111 cess in good overall yield, leading to novel pentacyclic products.

112 , with production of tetracyclic rather than pentacyclic products.

113 The reaction forming a pentacyclic propellane was calculated to have DeltaH = -

114 The common pentacyclic pyrrolodihydroisoquinoline lactone/lactam co

115 ed in solution in complex with a fluorinated pentacyclic quino[4,3,2-kl]acridinium cation (RHPS4).

116 Two short routes to novel methylated pentacyclic quinoacridinium salts have been devised.

117 A small library of pentacyclic quinoid compounds, called KuQuinones (KuQs),

118 inear array of 10 five-membered rings in two pentacyclic regions that derive from ribosomal peptide s

119 a decarboxylation step to form the 6/5/5/6/6 pentacyclic ring in 21R-citrinadin A.

120 -oxadiazole that provided the functionalized pentacyclic ring system 15 in a single step in which the

121 15, which provided the highly functionalized pentacyclic ring system in one step as a single diastere

122 nds are formed central to the characteristic pentacyclic ring system setting all six stereocenters an

123 hree rings and four C-C bonds central to the pentacyclic ring system setting all six stereocenters an

124 hree rings and four C-C bonds central to the pentacyclic ring system setting all six stereocenters an

125 erpenoids featuring a unique 6/5/5/9/4 fused pentacyclic ring system were isolated from Rhodomyrtus t

126 olefin dipolar cycloaddition to complete the pentacyclic ring system.

127 d 2 possess an unprecedented 5/5/7/5/5-fused pentacyclic ring system.

128 metabolite with a previously uncharacterized pentacyclic ring system.

129 broad tolerance towards substitutions in the pentacyclic ring that acted as a plug of the active site

130 Double bond isomerization between the two pentacyclic rings in 1,2-dihydropentalenes with electron

131 nin A possesses a unique cage-like 5/5/5/5/5 pentacyclic scaffold containing a trans-pentalene and a

132 novel class of Aurora inhibitors based on a pentacyclic scaffold.

133 nd cleavage/C-N bond formation furnished the pentacyclic scaffold.

134 fused pyrrolo[1,2-a]quinoline (tricyclic to pentacyclic scaffolds) by the construction of both pyrro

135 l-type sesterterpenes with tri-, tetra-, and pentacyclic scaffolds, and notably (-)-ent-quiannulatene

136 ents are identified as spiroborates with two pentacyclic sec-butyl-trihydroxy-methyl-benzo[gh]tetraph

137 ynthesis of (+)-punctaporonin U, a cage-like pentacyclic sesquiterpene bearing eight contiguous stere

138 enes, revealing the cyclization path for the pentacyclic sesterterpene (-)-retigeranin B.

139 n cascade of a 1,3,4-oxadiazole in which the pentacyclic skeleton and all the stereochemistry of the

140 This meroterpenoid features a unique pentacyclic skeleton distinguished by a fused 6/6/6 dihy

141 ype Ergot alkaloid noteworthy for its unique pentacyclic skeleton featuring a 3-azabicyclo[3.1.0]hexa

142 n alpha-diazo indoloamide which delivers the pentacyclic skeleton of the natural product in excellent

143 -scholarisine G (9) with a [6.5.6.6.5] fused pentacyclic skeleton, respectively.

144 roblem of assembling the final D-ring of the pentacyclic skeleton.

145 Detailed experimental approaches toward the pentacyclic Stemona alkaloids tuberostemonine and didehy

146 Reduction of these enones gave the pentacyclic steroidal ketones 2 alpha,3beta- (8) and 2 a

147 cation-pi cyclization stages to generate the pentacyclic structure with complete stereocontrol.

148 oxidations at different positions across the pentacyclic structure.

149 ation that converts the cyclopentenes to the pentacyclic structures of the natural products.

150 ives utilized Pummerer chemistry to generate pentacyclic structures related to the palau'amine family

151 oles 15, 22, and 26 and their elaboration to pentacyclic structures via a conjugate addition, dipolar

152 We have synthesized four novel pentacyclic Strychnos alkaloids alstolucines B (2), F (3

153 lding conversion of the ABDE tetracycle into pentacyclic target rac-1 relied on intramolecular indole

154 ic therapeutic plant Boswellia serrata, is a pentacyclic terpenoid active against a large number of i

155 oleum biomarkers (steranes, diasteranes, and pentacyclic triterpanes) naturally occurring in crude oi

156 n-alkanes, polycyclic aromatic hydrocarbons, pentacyclic triterpanes, compound specific isotope analy

157 Ursolic acid, a pentacyclic triterpene acid, has been shown to suppress

158 ed light on the spatiotemporal regulation of pentacyclic triterpene biosynthesis in sweet basil.

159 ing methods, we discovered that Celastrol, a pentacyclic triterpene extracted from the roots of Tript

160 UA is a pentacyclic triterpene found too in several traditional

161 Maslinic acid, a pentacyclic triterpene from Olea europaea L., exerts hyp

162 key intermediate 2 for the synthesis of the pentacyclic triterpene germanicol 1 have been developed.

163 Betulinic acid (BA), a pentacyclic triterpene isolated from the bark of the whi

164 iacin (olean-18-en-3beta-ol methyl ether), a pentacyclic triterpene methyl ether that is enriched in

165 Miliacin, a pentacyclic triterpene methyl ether uniquely abundant in

166 Betulinic acid is a pentacyclic triterpene natural product initially identif

167 e of modifying both the C and D rings of the pentacyclic triterpene scaffold to give 12,13beta-epoxy-

168 t that celastrol, a potent anti-inflammatory pentacyclic triterpene, binds Nur77 to inhibit inflammat

169 Lupeol, a pentacyclic triterpene, from the hexane extract of Solan

170 Celastrol, a pentacyclic triterpene, is the most potent antiobesity a

171 Among the latter, the group of pentacyclic triterpenes (PcTr) is the least studied.

172 Previous studies suggest that pentacyclic triterpenes (PCTs), a class of plant-derived

173 Pentacyclic triterpenes are minor, but very relevant com

174 r the simultaneous determination of the main pentacyclic triterpenes from Olea europaea L. in rat pla

175 greater than that of OA, and consumption of pentacyclic triterpenes was associated with improved end

176 ablished using artificially mixed samples of pentacyclic triterpenes which were screened for modulato

177 elin, the most drastically rearranged of the pentacyclic triterpenes, involves a complex nonstop proc

178 precursors of oleanane-type and ursane-type pentacyclic triterpenes, respectively.

179 d squalene (8-fold) and was a good source of pentacyclic triterpenes.

180 ally important ursane-type and oleanane-type pentacyclic triterpenes.

181 eering strategies for enhanced production of pentacyclic triterpenes.

182 Table olives are especially rich in pentacyclic triterpenic compounds, which exert several b

183 h displays equal or greater potency than the pentacyclic triterpenoid CDDO in inflammation and carcin

184 strength, quality, and mass: ursolic acid (a pentacyclic triterpenoid found in apples) and tomatidine

185 estigated the effect of ursolic acid (UA), a pentacyclic triterpenoid found in rosemary and holy basi

186 re, we report the identification of escin, a pentacyclic triterpenoid from horse chestnut that exhibi

187 high-throughput screening, we identified the pentacyclic triterpenoid hederagenin (1) as a novel sele

188 Oleanolic acid (OA), a pentacyclic triterpenoid, has been shown to modulate mul

189 The effects of a pentacyclic triterpenoid, methyl 2-trifluoromethyl-3,11-

190 ds, only ursolic acid, a naturally occurring pentacyclic triterpenoid, successfully inhibited binding

191 ys, the simple structure is more potent than pentacyclic triterpenoids (e.g., CDDO and bardoxolone me

192 Various ursanic, oleanic and lupanic pentacyclic triterpenoids found in apple peel were studi

193 Structurally related pentacyclic triterpenoids methyl 2-cyano-3,12-dioxoolean

194 Sedimentary hopanes are pentacyclic triterpenoids that serve as biomarker proxie

195 Pentacyclic triterpenoids, including ursolic acid (UA),

196 5%) of non-polar extractables from cork were pentacyclic triterpenoids, primarily betulinic acid, fri

197 l one-pot transformation of dialdehyde 24 to pentacyclic unsaturated amine 25.