ISSN:
0947-3440
Keywords:
Heck reaction, enantioselective
;
Allylsilanes
;
Norsesquiterpenes
;
7-Demethyl-2-methoxycalamenene, total synthesis, absolute configuration, and cytotoxicity of
;
Chemistry
;
Organic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
The total synthesis of the norsesquiterpene 7-demethyl-2-methoxycalamenene (1) by a newly developed enantioselective silane-terminated Heck reaction is described. The Pd0-catalyzed transformation of the allylsilane 7, obtained from 3-(3-methoxyphenyl)propanol (2) in 7 steps, provides the tetralin 8 in 91% yield and with 92% ee in the presence of (R)-BINAP. Transformation of 8 via 14 and 15 gives 1. The absolute configuration of 1 which has previously not been known was deduced from a single-crystal X-ray analysis of 10, obtained from the cyclization product 8 by hydroboration and acylation with camphanic acid chloride.
Additional Material:
1 Ill.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/jlac.199619961207
