Stereoselective total synthesis of preclavulone-A methyl ester and its diastereomer

被引：7

作者：

Ito, H ^{[1
]}

Konishi, M ^{[1
]}

Iguchi, K ^{[1
]}

机构：

[1] Tokyo Univ Pharm & Life Sci, Sch Life Sci, Tokyo 1920392, Japan

来源：

TETRAHEDRON LETTERS | 2004年 / 45卷 / 09期

关键词：

D O I：

10.1016/j.tetlet.2003.12.140

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The total synthesis of preclavulone-A methyl ester and its diastereomer was achieved from same key intermediate in diastereoselective manner. These compounds are recognized as important intermediates in a proposed biosynthesis of marine prostanoids from the Okinawan soft coral, Clavularia viridis, and were recently isolated from the extract of C. viridis by our group. (C) 2004 Elsevier Ltd. All rights reserved.

引用

页码：1941 / 1944

页数：4

共 15 条

[1] IDENTIFICATION OF A NEW EICOSANOID FROM INVITRO BIOSYNTHETIC EXPERIMENTS WITH CLAVULARIA-VIRIDIS - IMPLICATIONS FOR THE BIOSYNTHESIS OF CLAVULONES
COREY, EJ
LANSBURY, PT
YAMADA, Y
[J]. TETRAHEDRON LETTERS, 1985, 26 (35) : 4171 - 4174
[2] INTERMEDIACY OF 8-(R)-HPETE IN THE CONVERSION OF ARACHIDONIC-ACID TO PRE-CLAVULONE-A BY CLAVULARIA-VIRIDIS - IMPLICATIONS FOR THE BIOSYNTHESIS OF MARINE PROSTANOIDS
COREY, EJ
DALARCAO, M
MATSUDA, SPT
LANSBURY, PT
YAMADA, Y
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1987, 109 (01) : 289 - 290
[3] ENANTIOSELECTIVE TOTAL SYNTHESIS OF (-)-PRECLAVULONE-A
COREY, EJ
XIANG, YB
[J]. TETRAHEDRON LETTERS, 1988, 29 (09) : 995 - 998
[4] CATALYTIC RING-CLOSING METATHESIS OF FUNCTIONALIZED DIENES BY A RUTHENIUM CARBENE COMPLEX
FU, GC
NGUYEN, ST
GRUBBS, RH
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (21) : 9856 - 9857
[5] Recent advances in olefin metathesis and its application in organic synthesis
Grubbs, RH
Chang, S
[J]. TETRAHEDRON, 1998, 54 (18) : 4413 - 4450
[6] CLAVULONES, NEW TYPE OF PROSTANOIDS FROM THE STOLONIFER CLAVULARIA-VIRIDIS QUOY AND GAIMARD
KIKUCHI, H
TSUKITANI, Y
IGUCHI, K
YAMADA, Y
[J]. TETRAHEDRON LETTERS, 1982, 23 (49) : 5171 - 5174
[7] ABSOLUTE STEREOCHEMISTRY OF NEW PROSTANOIDS CLAVULONE-I, CLAVULONE-II AND CLAVULONE-III, FROM CLAVULARIA-VIRIDIS QUOY AND GAIMARD
KIKUCHI, H
TSUKITANI, Y
IGUCHI, K
YAMADA, Y
[J]. TETRAHEDRON LETTERS, 1983, 24 (14) : 1549 - 1552
[8] Kim B. M., 1991, COMPREHENSIVE ORGANI, V2
[9] MARINE NATURAL-PRODUCTS .13. NEW PROSTANOIDS FROM SOFT CORAL
KITAGAWA, I
KOBAYASHI, M
YASUZAWA, T
SON, BW
YOSHIHARA, M
KYOGOKU, Y
[J]. TETRAHEDRON, 1985, 41 (06) : 995 - 1005
[10] 4 NEW PROSTANOIDS - CLAVIRIDENONE-A, CLAVIRIDENONE-B, CLAVIRIDENONE-C, AND CLAVIRIDENONE-D FROM THE OKINAWAN SOFT CORAL CLAVULARIA-VIRIDIS
KOBAYASHI, M
YASUZAWA, T
YOSHIHARA, M
AKUTSU, H
KYOGOKU, Y
KITAGAWA, I
[J]. TETRAHEDRON LETTERS, 1982, 23 (50) : 5331 - 5334

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