[3,3]SIGMATROPIC RING EXPANSION OF CYCLIC THIONOCARBONATES .9. TOTAL SYNTHESIS OF (+ -)-YELLOW SCALE PHEROMONE VIA 10-MEMBERED THIOLCARBONATE/

Authors
HARUSAWA S TAKEMURA S OSAKI H YONEDA R KURIHARA T
Citation
S. Harusawa et al., [3,3]SIGMATROPIC RING EXPANSION OF CYCLIC THIONOCARBONATES .9. TOTAL SYNTHESIS OF (+ -)-YELLOW SCALE PHEROMONE VIA 10-MEMBERED THIOLCARBONATE/, Tetrahedron, 49(35), 1993, pp. 7657-7666
Citations number
23
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron → ACNP
ISSN journal
00404020
Volume
49
Issue
35
Year of publication
1993
Pages
7657 - 7666
Database
ISI
SICI code
0040-4020(1993)49:35<7657:[REOCT>2.0.ZU;2-B
Abstract
(+/-)-Yellow scale pheromone 1 has been synthesized via the route illu strated in Scheme 1. The [3,3]sigmatropic ring expansion of 8-membered thionocarbonate 4 exclusively produced the (Z)-10-membered thiolcarbo nate 3, which was transformed via three steps to the intermediate 2 wi th all the necessary carbon atoms for the pheromone. Reductive removal of the SCO moiety in 2 followed by acetylation gave 1.