Synthesis of dendryphiellin C, a trinor-sesquiterpene from a marine source

被引：14

作者：

Akao, H ^{[1
]}

Kiyota, H ^{[1
]}

Nakajima, T ^{[1
]}

Kitahara, T ^{[1
]}

机构：

[1] Univ Tokyo, Grad Sch Agr & Life Sci, Dept Appl Biol Chem, Bunkyo Ku, Tokyo 1138657, Japan

来源：

TETRAHEDRON | 1999年 / 55卷 / 25期

关键词：

D O I：

10.1016/S0040-4020(99)00407-X

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Enantioselective synthesis of dendryphiellin C, isolated from cultures of Dendryphiella sarina, has been achieved in a convergent way such as coupling of a C9-branched carboxylic acid 10 with a trinor-eremophilane alcohol 11. The latter was synthesized starting from a chiral building block, (1S,5S,6R)-5-hydroxybicyclo[4.1.0]heptan-2-one 16, which was originally prepared in this group using biochemical transformation as a key step. The synthesis was completed through 12 steps from 16 in overall 2.4% yield. (C) 1999 Elsevier Science Ltd. All rights reserved.

引用

页码：7757 / 7770

页数：14

共 20 条

[1] BOECKMAN RK, 1973, ORG SYNTH, V5, P1033
[2] CHEMISTRY OF OXAZIRIDINES .2. IMPROVED SYNTHESIS OF 2-SULFONYLOXAZIRIDINES
DAVIS, FA
STRINGER, OD
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1982, 47 (09) : 1774 - 1775
[3] SYNTHESIS OF ALPHA-HYDROXY CARBONYL-COMPOUNDS (ACYLOINS) - DIRECT OXIDATION OF ENOLATES USING 2-SULFONYLOXAZIRIDINES
DAVIS, FA
VISHWAKARMA, LC
BILLMERS, JM
FINN, J
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1984, 49 (17) : 3241 - 3243
[4] DENDRYPHIELLIN-A, THE 1ST FUNGAL TRINOR-EREMOPHILANE - ISOLATION FROM THE MARINE DEUTEROMYCETE DENDRYPHIELLA-SALINA (SUTHERLAND) PUGH AND NICOT
GUERRIERO, A
DAMBROSIO, M
CUOMO, V
VANZANELLA, F
PIETRA, F
[J]. HELVETICA CHIMICA ACTA, 1988, 71 (01) : 57 - 61
[5] A NOVEL GLYCERYL ESTER (GLYCERYL DENDRYPHIELLATE-A), A TRINOR-EREMOPHILANE (DENDRYPHIELLIN-A1), AND EREMOPHILANES (DENDRYPHIELLIN-E1 AND DENDRYPHIELLIN-E2) FROM THE MARINE DEUTEROMYCETE DENDRYPHIELLA-SALINA (SUTHERLAND) PUGH AND NICOT
GUERRIERO, A
CUOMO, V
VANZANELLA, F
PIETRA, F
[J]. HELVETICA CHIMICA ACTA, 1990, 73 (08) : 2090 - 2096
[6] GUERRIERO A, 1989, HELV CHIM ACTA, V72
[7] RAPID ESTERIFICATION BY MEANS OF MIXED ANHYDRIDE AND ITS APPLICATION TO LARGE-RING LACTONIZATION
INANAGA, J
HIRATA, K
SAEKI, H
KATSUKI, T
YAMAGUCHI, M
[J]. BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1979, 52 (07) : 1989 - 1993
[8] A BRASSINOLIDE-INHIBITOR KM-01, ITS ISOLATION AND STRUCTURE ELUCIDATION FROM A FUNGUS DRECHSLERA-AVENAE
KIM, SK
MIZUNO, K
HATORI, M
MARUMO, S
[J]. TETRAHEDRON LETTERS, 1994, 35 (11) : 1731 - 1734
[9] SYNTHESIS OF MONOTERPENOIDS AND SESQUITERPENOIDS .20. SYNTHESIS OF OXYGENATED EREMOPHILANES, GIGANTENONE, PHOMENONE AND PHASEOLINONE, PHYTOTOXINS FROM PATHOGENIC FUNGI
KITAHARA, T
KIYOTA, H
KURATA, H
MORI, K
[J]. TETRAHEDRON, 1991, 47 (09) : 1649 - 1654
[10] SYNTHETIC MICROBIAL CHEMISTRY .18. EFFICIENT SYNTHESIS OF THE NATURAL ENANTIOMER OF SPOROGEN-AO-1 (13-DESOXYPHOMENONE), A SPOROGENIC SESQUITERPENE FROM ASPERGILLUS-ORYZAE
KITAHARA, T
KURATA, H
MORI, K
[J]. TETRAHEDRON, 1988, 44 (14) : 4339 - 4349

← 1 2 →