A new general method for the synthesis of polyenes involving 1,6-, 1,8-, 1,10-and 1,12-carbonyl group transpositions via alpha-oxoketene dithioacetals

Authors
Satyanarayana, J Siddiqui, I Ila, H Junjappa, H
Citation
J. Satyanarayana et al., A new general method for the synthesis of polyenes involving 1,6-, 1,8-, 1,10-and 1,12-carbonyl group transpositions via alpha-oxoketene dithioacetals, I J CHEM B, 40(10), 2001, pp. 948-954
Citations number
6
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
INDIAN JOURNAL OF CHEMISTRY SECTION B-ORGANIC CHEMISTRY INCLUDING MEDICINAL CHEMISTRY
ISSN journal
03764699 → ACNP
Volume
40
Issue
10
Year of publication
2001
Pages
948 - 954
Database
ISI
SICI code
0376-4699(200110)40:10<948:ANGMFT>2.0.ZU;2-1
Abstract
A novel strategy for hitherto unreported even numbered i.e. 1,6 -, 1,8-, 1, 10- and 1,12-carbonyl transpositions has been demonstrated on newly synthes ized model cyclopropyl polyenones 2a-h by subjecting them to either 1,2- re duction or 1,2-alkylative addition followed by solvolysis in the presence o f BF3.Et2O/HgCl2/MeOH to give novel polyene esters 4a-h, 10h and 10g in hig hly regio- and stereoselective manner.