Enantioselective synthesis of (-)-LL-C10037 alpha from benzoquinone

Authors
Murphy, ST Bencsik, JR Johnson, CR
Citation
St. Murphy et al., Enantioselective synthesis of (-)-LL-C10037 alpha from benzoquinone, ORG LETT, 1(9), 1999, pp. 1483-1485
Citations number
37
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
ORGANIC LETTERS
ISSN journal
15237060 → ACNP
Volume
1
Issue
9
Year of publication
1999
Pages
1483 - 1485
Database
ISI
SICI code
1523-7060(19991104)1:9<1483:ESO(AF>2.0.ZU;2-A
Abstract
The enantioselective total synthesis of the Streptomyces metabolite (-)-LL- C10037 alpha has been accomplished in 10 steps and 20% overall yield. An ea rly chiral intermediate was resolved with Candida rugosa lipase to provide (+)-5 with an enantiomeric excess greater than or equal to 98%. The synthes is is notable in that no protecting groups are required and that all carbon s in the core structure of LL-C10037 alpha are derived from the readily ava ilable p-benzoquinone.