An expeditious synthesis of (+/-)-desepoxy-4,5-didehydromethylenomycin A methyl ester

Authors
Balczewski, P Mikolajczyk, M
Citation
P. Balczewski et M. Mikolajczyk, An expeditious synthesis of (+/-)-desepoxy-4,5-didehydromethylenomycin A methyl ester, ORG LETT, 2(8), 2000, pp. 1153-1155
Citations number
27
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
ORGANIC LETTERS
ISSN journal
15237060 → ACNP
Volume
2
Issue
8
Year of publication
2000
Pages
1153 - 1155
Database
ISI
SICI code
1523-7060(20000420)2:8<1153:AESO(A>2.0.ZU;2-5
Abstract
A total synthesis of the racemic methyl ester of desepoxy-4,5-didehydrometh ylenomycin A has been achieved in six steps with an overall yield of 31% st arting from diethyl methanephosphonate. The key steps include the Nazarov c yclization of the dienone 7 leading to the alpha-phosphoryl cyclopentenone 8 and the Horner-Wittig reaction of the latter employed for the introductio n of the exocyclic methylene moiety.