Synthesis of the central C18-C30 core of the phorboxazole natural products

被引:60
作者
Lee, CS [1 ]
Forsyth, CJ [1 ]
机构
[1] UNIV MINNESOTA,DEPT CHEM,MINNEAPOLIS,MN 55455
关键词
D O I
10.1016/0040-4039(96)01435-9
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A direct synthesis of the central C18-C30 core of the phorboxazole natural products has been developed. This involves construction of an acyclic acrylate using Paterson's (E)-enol borinate aldol methodology followed by an intramolecular hetero-Michael addition to form the central pyran ring of the natural products. Copyright (C) 1996 Elsevier Science Ltd
引用
收藏
页码:6449 / 6452
页数:4
相关论文
共 9 条
[1]   SYNTHETIC STUDIES TOWARDS HALICHONDRINS [J].
AICHER, TD ;
KISHI, Y .
TETRAHEDRON LETTERS, 1987, 28 (30) :3463-3466
[2]   HORNER-WADSWORTH-EMMONS REACTION - USE OF LITHIUM-CHLORIDE AND AN AMINE FOR BASE SENSITIVE COMPOUNDS [J].
BLANCHETTE, MA ;
CHOY, W ;
DAVIS, JT ;
ESSENFELD, AP ;
MASAMUNE, S ;
ROUSH, WR ;
SAKAI, T .
TETRAHEDRON LETTERS, 1984, 25 (21) :2183-2186
[3]   A USEFUL 12-I-5 TRIACETOXYPERIODINANE (THE DESS-MARTIN PERIODINANE) FOR THE SELECTIVE OXIDATION OF PRIMARY OR SECONDARY ALCOHOLS AND A VARIETY OF RELATED 12-I-5 SPECIES [J].
DESS, DB ;
MARTIN, JC .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (19) :7277-7287
[4]   DIRECTED REDUCTION OF BETA-HYDROXY KETONES EMPLOYING TETRAMETHYLAMMONIUM TRIACETOXYBOROHYDRIDE [J].
EVANS, DA ;
CHAPMAN, KT ;
CARREIRA, EM .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1988, 110 (11) :3560-3578
[5]   THE SYNTHESIS AND CONFIGURATIONAL STABILITY OF DIFFERENTIALLY PROTECTED BETA-HYDROXY-ALPHA-AMINO ALDEHYDES [J].
GARNER, P ;
PARK, JM .
JOURNAL OF ORGANIC CHEMISTRY, 1987, 52 (12) :2361-2364
[6]   MPM (4-METHOXYBENZYL) PROTECTION OF HYDROXY FUNCTIONS UNDER MILD ACIDIC CONDITIONS [J].
NAKAJIMA, N ;
HORITA, K ;
ABE, R ;
YONEMITSU, O .
TETRAHEDRON LETTERS, 1988, 29 (33) :4139-4142
[7]   ALDOL REACTIONS IN POLYPROPIONATE SYNTHESIS - HIGH PI-FACE SELECTIVITY OF ENOL BORINATES FROM ALPHA-CHIRAL METHYL AND ETHYL KETONES UNDER SUBSTRATE CONTROL [J].
PATERSON, I ;
GOODMAN, JM ;
ISAKA, M .
TETRAHEDRON LETTERS, 1989, 30 (50) :7121-7124
[8]   ALDOL CONDENSATIONS OF CHIRAL ETHYLKETONES - CONTROL BY CHIRAL BORON REAGENTS [J].
PATERSON, I ;
LISTER, MA .
TETRAHEDRON LETTERS, 1988, 29 (05) :585-588
[9]  
SEARLE PA, 1995, J AM CHEM SOC, V117, P8216