Synthesis of highly substituted 2,6-anti-configured tetrahydropyrans.: First steps towards an efficient access to amphidinol 3 ring system

被引：30

作者：

Dubost, C

Markó, IE

Bryans, J

机构：

[1] Catholic Univ Louvain, Dept Chim, Unite Chim Organ & Med, B-1348 Louvain, Belgium

[2] Pfizer Ltd, Global Res & Dev, Sandwich CT13 9NJ, Kent, England

来源：

TETRAHEDRON LETTERS | 2005年 / 46卷 / 23期

关键词：

tetrahydropyrans; amphidinols; Sakurai reaction; allylation; tin;

D O I：

10.1016/j.tetlet.2005.04.041

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Highly functionalised and polysubstituted tetrahydropyrans, akin to the middle core of the amphidinols, can be efficiently synthesised, with full stereocontrol and in good yields, using as key steps an anti-allylation reaction coupled with an intramolecular Sakurai cyclisation. Three approaches were devised in order to reach a broad range of substitution patterns. (c) 2005 Elsevier Ltd. All rights reserved.

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收藏

页码：4005 / 4009

页数：5

相关论文

共 17 条

[1] Chemoselective cross-metathesis reaction. Application to the synthesis of the C1-C14 fragment of amphidinol 3 [J].

BouzBouz, S ;

Cossy, J .

ORGANIC LETTERS, 2001, 3 (10) :1451-1454

[2] Stereoselective synthesis of functionalised triol units by SnCl4 promoted allylation of α-benzyloxyaldehydes:: crucial role of the stoichiometry of the Lewis acid [J].

Dubost, C ;

Leroy, B ;

Markó, IE ;

Tinant, B ;

Declercq, JP ;

Bryans, J .

TETRAHEDRON, 2004, 60 (35) :7693-7704

[3] Synthetic studies directed toward the phorboxazoles: preparation of the C3-C15 bisoxane segment and two stereoisomers [J].

Greer, PB ;

Donaldson, WA .

TETRAHEDRON, 2002, 58 (30) :6009-6018

[4] Lingshuiols A and B, two new polyhydroxy compounds from the Chinese marine dinoflagellate Amphidinium sp. [J].

Huang, XC ;

Zhao, D ;

Guo, YW ;

Wu, HM ;

Trivellone, E ;

Cimino, G .

TETRAHEDRON LETTERS, 2004, 45 (28) :5501-5504

[5] Stereocontrolled synthesis and reactivity of sugar acetylenes [J].

Isobe, M ;

Nishizawa, R ;

Hosokawa, S ;

Nishikawa, T .

CHEMICAL COMMUNICATIONS, 1998, (24) :2665-2676

[6]

Krief A, 1998, SYNLETT, P1219

[7] Efficient and stereocontrolled synthesis of polysubstituted tetrahydropyrans by an allylstannylation/Bi(III)-promoted cyclisation strategy [J].

Leroy, B ;

Markó, IE .

TETRAHEDRON LETTERS, 2001, 42 (49) :8685-8688

[8] HIGHLY STEREOSELECTIVE APPROACHES TO ALPHA-C-GLYCOPYRANOSIDE AND BETA-C-GLYCOPYRANOSIDE [J].

LEWIS, MD ;

CHA, JK ;

KISHI, Y .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1982, 104 (18) :4976-4978

[9] ISOLATION AND STRUCTURE OF BREVETOXIN-B FROM THE RED TIDE DINOFLAGELLATE PTYCHODISCUS-BREVIS (GYMNODINIUM, BREVE) [J].

LIN, YY ;

RISK, M ;

RAY, SM ;

VANENGEN, D ;

CLARDY, J ;

GOLIK, J ;

JAMES, JC ;

NAKANISHI, K .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1981, 103 (22) :6773-6775

[10]

Markó IE, 2002, SYNTHESIS-STUTTGART, P958