Absolute configuration of phorboxazole A C32-C43 analogs by CD exciton-coupling of allylic 2-naphthoate esters

被引:19
作者
Molinski, TF
Brzezinski, LJ
Leahy, JW
机构
[1] Univ Calif Davis, Dept Chem, Davis, CA 95616 USA
[2] Univ Calif Berkeley, Dept Chem, Berkeley, CA 94720 USA
基金
美国国家卫生研究院;
关键词
D O I
10.1016/S0957-4166(02)00234-3
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
The configurations of phorboxazole model compounds 4a and 4b were assigned as (33R,35S,37S,38S) and (33R,35S,37S,38R), respectively, by analysis of exciton coupling in the corresponding 2-naphthoate esters. Spectroscopic comparisons with phorboxazoles A and B provides independent proof of the 38R absolute configuration of these natural products. (C) 2002 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:1013 / 1016
页数:4
相关论文
共 19 条
[1]  
Evans DA, 2000, ANGEW CHEM INT EDIT, V39, P2533, DOI 10.1002/1521-3773(20000717)39:14<2533::AID-ANIE2533>3.0.CO
[2]  
2-B
[3]  
Evans DA, 2000, ANGEW CHEM INT EDIT, V39, P2536, DOI 10.1002/1521-3773(20000717)39:14<2536::AID-ANIE2536>3.0.CO
[4]  
2-U
[5]   Application of complex aldol reactions to the total synthesis of phorboxazole B [J].
Evans, DA ;
Fitch, DM ;
Smith, TE ;
Cee, VJ .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (41) :10033-10046
[6]   Total synthesis of phorboxazole A [J].
Forsyth, CJ ;
Ahmed, F ;
Cink, RD ;
Lee, CS .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (22) :5597-5598
[7]   GENERAL-METHOD FOR DETERMINING ABSOLUTE-CONFIGURATIONS OF ACYCLIC ALLYLIC ALCOHOLS [J].
GONNELLA, NC ;
NAKANISHI, K ;
MARTIN, VS ;
SHARPLESS, KB .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1982, 104 (13) :3775-3776
[8]  
HAMEL E, COMMUNICATION
[9]  
Harada N., 1983, CIRCULAR DICHROIC SP
[10]   Absolute configuration of phorboxazoles A and B from the marine sponge, Phorbas sp .2. C43 and complete stereochemistry [J].
Molinski, TF .
TETRAHEDRON LETTERS, 1996, 37 (44) :7879-7880