Enzymatic kinetic resolution of primary allenic alcohols. Application to the total synthesis and stereochemical assignment of striatisporolide A

Jan Deska; Jan-E. Bäckvall

doi:10.1039/B912128P

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Organic & Biomolecular Chemistry

Issue 17, 2009

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Enzymatic kinetic resolution of primary allenic alcohols. Application to the total synthesis and stereochemical assignment of striatisporolide A

Jan Deska and Jan-E. Bäckvall

Org. Biomol. Chem., 2009, 7, 3379-3381

DOI: 10.1039/B912128P
Received 19 Jun 2009, Accepted 29 Jun 2009
First published on the web 09 Jul 2009

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Crude Porcine pancreatic lipase was successfully used for the kinetic resolution of axially chiral primary allenic alcohols providing very high enantioselectivities with E values above 200. This simple access to optically active allenes was applied to the total synthesis of the fungal metabolite (−)-striatisporolide A, allowing its unambiguous stereochemical assignment.

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Organic & Biomolecular Chemistry

Enzymatic kinetic resolution of primary allenic alcohols. Application to the total synthesis and stereochemical assignment of striatisporolide A

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