Biosynthesis of C11 and C16 homoterpenes in higher plants;: Stereochemistry of the C-C-bond cleavage reaction

被引：36

作者：

Boland, W ^{[1
]}

Gäbler, A ^{[1
]}

Gilbert, M ^{[1
]}

Feng, ZF ^{[1
]}

机构：

[1] Max Planck Inst Chem Okol, D-07745 Jena, Germany

来源：

TETRAHEDRON | 1998年 / 54卷 / 49期

关键词：

D O I：

10.1016/S0040-4020(98)00902-8

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

In higher plants the C-11 homoterpene 4,8-dimethylnona-1,3,7-triene (1) originates from oxidative degradation of nerolidol (3) or geranylacetone (4). The geometry of the transition state of bond cleavage has been shown to be syn-periplanar, for both 3 and 4 by application of chirally labelled, deuterated precursors to flowers of Magnolia liliiflora nigra or leaves of the Lima bean Phaseolus lunatus. The synthesis of the deuterated, chiral metabolic probes 3 and 8 from nor-farnesene (5), via the enantiomeric epoxides (2S,3R)-6 and ent-6, is described. (C) 1998 Elsevier Science Ltd. All rights reserved.

引用

页码：14725 / 14736

页数：12

共 28 条

[1] A UNIFIED MECHANISTIC VIEW OF OXIDATIVE REACTIONS CATALYZED BY P-450 AND RELATED FE-CONTAINING ENZYMES [J].