Catalytic enantioselective synthesis of naturally occurring butenolides via hetero-allylic alkylation and ring closing metathesis.

TitleCatalytic enantioselective synthesis of naturally occurring butenolides via hetero-allylic alkylation and ring closing metathesis.
Publication TypeJournal Article
Year of Publication2011
AuthorsMao B, Geurts K, Fañanás-Mastral M, van Zijl AW, Fletcher SP, Minnaard AJ, Feringa BL
JournalOrganic letters
Volume13
Issue5
Pagination948-51
Date Published2011 Mar 4
Abstract

An efficient catalytic asymmetric synthesis of chiral γ-butenolides was developed based on the hetero-allylic asymmetric alkylation (h-AAA) in combination with ring closing metathesis (RCM). The synthetic potential of the h-AAA-RCM protocol was illustrated with the facile synthesis of (-)-whiskey lactone, (-)-cognac lactone, (-)-nephrosteranic acid, and (-)-roccellaric acid.

DOI10.1152/ajpcell.00277.2012
Alternate JournalOrg. Lett.