Formal total synthesis of hemibrevetoxin B by a convergent strategy

被引：31

作者：

Fujiwara, K ^{[1
]}

Sato, D ^{[1
]}

Watanabe, M ^{[1
]}

Morishita, H ^{[1
]}

Murai, A ^{[1
]}

Kawai, H ^{[1
]}

Suzuki, T ^{[1
]}

机构：

[1] Hokkaido Univ, Grad Sch Sci, Div Chem, Sapporo, Hokkaido 0600810, Japan

来源：

TETRAHEDRON LETTERS | 2004年 / 45卷 / 27期

关键词：

polyether; hemibrevetoxin B; natural product synthesis; acyl anion equivalent; convergent synthesis;

D O I：

10.1016/j.tetlet.2004.05.020

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Concise construction of the trans-fused 7/7/6/6 tetracyclic ether part of hemibrevetoxin B (1) was achieved by a convergent strategy based on coupling reaction of an acyl anion equivalent, reductive cyclization of an alpha,epsilon-dihydroxyketone, and introduction of a methyl group at the central ring junction by the Nicolaou method. The resultant tetracyclic ether was transformed into the known intermediate, which was already converted to 1 by the Yamamoto group, thereby completing the formal total synthesis of 1. (C) 2004 Elsevier Ltd. All rights reserved.

引用

页码：5243 / 5246

页数：4

共 41 条

[11] CATALYTIC ASYMMETRIC EPOXIDATION AND KINETIC RESOLUTION - MODIFIED PROCEDURES INCLUDING INSITU DERIVATIZATION [J].

GAO, Y ;

HANSON, RM ;

KLUNDER, JM ;

KO, SY ;

MASAMUNE, H ;

SHARPLESS, KB .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1987, 109 (19) :5765-5780

[12] Rational design of benzyl-type protecting groups allows sequential deprotection of hydroxyl groups by catalytic hydrogenolysis [J].

Gaunt, MJ ;

Yu, JQ ;

Spencer, JB .

JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (13) :4172-4173

[13] LANTHANOIDS IN ORGANIC-SYNTHESIS .6. THE REDUCTION OF ALPHA-ENONES BY SODIUM-BOROHYDRIDE IN THE PRESENCE OF LANTHANOID CHLORIDES - SYNTHETIC AND MECHANISTIC ASPECTS [J].

GEMAL, AL ;

LUCHE, JL .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1981, 103 (18) :5454-5459

[14]

HERRMANN JL, 1973, TETRAHEDRON LETT, V14, P4707

[15]

Ishihara J, 1996, SYNLETT, P363

[16]

KADOTA I, 1995, TETRAHEDRON LETT, V36, P5777, DOI 10.1016/0040-4039(95)01097-2

[17] Stereocontrolled total synthesis of hemibrevetoxin B [J].

Kadota, I ;

Yamamoto, Y .

JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (19) :6597-6606

[18] AN ALTERNATIVE PROCEDURE FOR THE ALUMINUM-MEDIATED CONVERSION OF ESTERS TO AMIDES [J].

LEVIN, JI ;

TUROS, E ;

WEINREB, SM .

SYNTHETIC COMMUNICATIONS, 1982, 12 (13) :989-993

[19]

MANCUSO AJ, 1978, J ORG CHEM, V43, P2048

[20] KINETIC RESOLUTION OF RACEMIC ALLYLIC ALCOHOLS BY ENANTIOSELECTIVE EPOXIDATION - A ROUTE TO SUBSTANCES OF ABSOLUTE ENANTIOMERIC PURITY [J].

MARTIN, VS ;

WOODARD, SS ;

KATSUKI, T ;

YAMADA, Y ;

IKEDA, M ;

SHARPLESS, KB .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1981, 103 (20) :6237-6240

← 1 2 3 4 5 →