A SCALEMIC SYNTHESIS OF THE SCOPADULCIC ACID SKELETON .1. AN EFFICIENT GAMMA-ALKYLATION AT C-9 IN ABIETANE FRAMEWORK AND SUBSEQUENT ALDOL REACTION

Authors
TAGAT JR MCCOMBIE SW PUAR MS
Citation
Jr. Tagat et al., A SCALEMIC SYNTHESIS OF THE SCOPADULCIC ACID SKELETON .1. AN EFFICIENT GAMMA-ALKYLATION AT C-9 IN ABIETANE FRAMEWORK AND SUBSEQUENT ALDOL REACTION, Tetrahedron letters, 37(47), 1996, pp. 8459-8462
Citations number
13
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron letters → ACNP
ISSN journal
00404039
Volume
37
Issue
47
Year of publication
1996
Pages
8459 - 8462
Database
ISI
SICI code
0040-4039(1996)37:47<8459:ASSOTS>2.0.ZU;2-I
Abstract
The first example of a carbon-carbon bond formation at C-9 in the abie tane framework via a highly practical gamma-alkylation of the enone 6 is reported. Attempted intra-molecular aldol reaction of the derived e none aldehyde 13 gave exclusively the undesired product 14. However, t he 12-methyl enone aldehyde 17 gave a trace of the desired aldol 19, b ond formation at C-7 still being the major pathway. Copyright (C) 1996 Elsevier Science Ltd