The efficient stereoselective synthesis of (2S,3R,4S,5S,6S,11E)-3-amino-6-methyl-12-(4-methoxyphenyl)-2,4,5-trihydroxydodec-11-enoic acid (AMMTD), a component of microsclerodermins of marine sponge origin, as its protected form

被引:27
作者
Sasaki, S
Hamada, Y
Shioiri, T
机构
[1] Chiba Univ, Fac Pharmaceut Sci, Inage Ku, Chiba 2638522, Japan
[2] Nagoya City Univ, Fac Pharmaceut Sci, Mizuho Ku, Nagoya, Aichi 4678603, Japan
关键词
D O I
10.1016/S0040-4039(99)00411-6
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The title acid, a component of microsclerodermins of marine sponge origin having five consecutive stereogenic centers, was efficiently synthesized as its protected form 1 from the alcohol 5 utilizing the stereoselective addition of anisole to the acetylenic triple bond and the anti-aldol reaction as key steps. (C) 1999 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:3187 / 3190
页数:4
相关论文
共 8 条
[1]   MICROSCLERODERMIN-A AND MICROSCLERODERMIN-B - ANTIFUNGAL CYCLIC-PEPTIDES FROM THE LITHISTID SPONGE MICROSCLERODERMA SP [J].
BEWLEY, CA ;
DEBITUS, C ;
FAULKNER, DJ .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (17) :7631-7636
[2]   NICKEL-CATALYZED OR PALLADIUM-CATALYZED CROSS COUPLING .31. PALLADIUM-CATALYZED OR NICKEL-CATALYZED REACTIONS OF ALKENYLMETALS WITH UNSATURATED ORGANIC HALIDES AS A SELECTIVE ROUTE TO ARYLATED ALKENES AND CONJUGATED DIENES - SCOPE, LIMITATIONS, AND MECHANISM [J].
NEGISHI, E ;
TAKAHASHI, T ;
BABA, S ;
VANHORN, DE ;
OKUKADO, N .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1987, 109 (08) :2393-2401
[3]   STUDIES IN POLYPROPIONATE SYNTHESIS - HIGH PI-FACE SELECTIVITY IN SYN AND ANTI ALDOL REACTIONS OF CHIRAL BORON ENOLATES OF LACTATE-DERIVED KETONES [J].
PATERSON, I ;
WALLACE, DJ ;
VELAZQUEZ, SM .
TETRAHEDRON LETTERS, 1994, 35 (48) :9083-9086
[4]   MANIPULATION OF THE ALDOL ADDUCTS FROM LACTATE-DERIVED KETONES - A VERSATILE CHIRAL AUXILIARY FOR THE ASYMMETRIC-SYNTHESIS OF BETA-HYDROXY CARBONYL-COMPOUNDS [J].
PATERSON, I ;
WALLACE, DJ .
TETRAHEDRON LETTERS, 1994, 35 (48) :9087-9090
[5]   Synthetic studies of microsclerodermins. A stereoselective synthesis of a core building block for (2S,3R,4S,5S,6S,11E)-3-amino-6-methyl-12-(4-methoxyphenyl)-2,4,5-trihydroxydodec-11-enoic acid (AMMTD) [J].
Sasaki, S ;
Hamada, Y ;
Shioiri, T .
TETRAHEDRON LETTERS, 1997, 38 (17) :3013-3016
[6]   Total synthesis of antillatoxin, an ichthyotoxic cyclic lipopeptide, having the proposed structure. What is the real structure of antillatoxin? [J].
Yokokawa, F ;
Shioiri, T .
JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (24) :8638-8639
[7]  
1998, 35 JAP PEPT S HELD S
[8]  
1997, 1 INT PEPT S HELD KY