Synthesis of (3aR,8S,8bS,2'R)-(+)-sorgolactone and its stereoisomers, the germination stimulant from Sorghum bicolor

被引：13

作者：

Mori, K

Matsui, J

机构：

[1] Department of Chemistry, Faculty of Science, Science University of Tokyo, Tokyo 162, Kagurazaka 1-3, Shinjuku-ku

来源：

TETRAHEDRON LETTERS | 1997年 / 38卷 / 45期

关键词：

D O I：

10.1016/S0040-4039(97)10078-8

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Methyl (S)-citronellate (2) was convened to (3aR,8S,8bS,2'R)-(+)-sorgolactone (1a) by employing the radical cyclization of 6 to 7 as the key-step. Three other stereoisomers (1b, 1c and 1d) of sorgolactone were also prepared. The CD spectrum of 1a was in accord with that reported for the natural product. (C) 1997 Elsevier Science Ltd.

引用

页码：7891 / 7892

页数：2

共 6 条

[1] FORMATION OF CARBON CARBON BONDS BY RING-CLOSURE OF BETA-PHENYLSELENOCROTONATES [J].

CLIVE, DLJ ;

BEAULIEU, PL .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1983, (06) :307-309

[2] A GERMINATION STIMULANT FOR PARASITIC FLOWERING PLANTS FROM SORGHUM-BICOLOR, A GENUINE HOST PLANT [J].

HAUCK, C ;

MULLER, S ;

SCHILDKNECHT, H .

JOURNAL OF PLANT PHYSIOLOGY, 1992, 139 (04) :474-478

[3] LANTHANIDES IN ORGANIC-CHEMISTRY .1. SELECTIVE 1,2 REDUCTIONS OF CONJUGATED KETONES [J].

LUCHE, JL .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1978, 100 (07) :2226-2227

[4] Synthesis and biological evaluation of the four racemic stereoisomers of the structure proposed for sorgolactone, the germination stimulant from Sorghum bicolor [J].

Mori, K ;

Matsui, J ;

Bando, M ;

Kido, M ;

Takeuchi, Y .

TETRAHEDRON LETTERS, 1997, 38 (14) :2507-2510

[5] Strigol and sorgolactone synthetic studies use of Winterfeldt's template to control the C-2' configuration [J].

Rohrig, S ;

Hennig, L ;

Findeisen, M ;

Welzel, P ;

Muller, D .

TETRAHEDRON LETTERS, 1997, 38 (31) :5489-5492

[6] The first total synthesis of the naturally occurring germination stimulant sorgolactone [J].

Sugimoto, Y ;

Wigchert, SCM ;

Thuring, JWJF ;

Zwanenburg, B .

TETRAHEDRON LETTERS, 1997, 38 (13) :2321-2324

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