BIOSYNTHESIS OF C-11 AND C-16 HOMOTERPENES IN HIGHER-PLANTS - STEREOCHEMISTRY OF THE C-C-BOND CLEAVAGE REACTION

Citation
W. Boland et al., BIOSYNTHESIS OF C-11 AND C-16 HOMOTERPENES IN HIGHER-PLANTS - STEREOCHEMISTRY OF THE C-C-BOND CLEAVAGE REACTION, Tetrahedron, 54(49), 1998, pp. 14725-14736
Citations number
27
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
ISSN journal
00404020
Volume
54
Issue
49
Year of publication
1998
Pages
14725 - 14736
Database
ISI
SICI code
0040-4020(1998)54:49<14725:BOCACH>2.0.ZU;2-2
Abstract
In higher plants the C-11 homoterpene 4,8-dimethylnona-1,3,7-triene (1 ) originates from oxidative degradation of nerolidol (3) or geranylace tone (4). The geometry of the transition state of bond cleavage has be en shown to be syn-periplanar, for both 3 and 4 by application of chir ally 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.