Enantioselective Total Synthesis of (-)-Dactylolide

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Org. Lett., 8 (6), 1117 -1120, 2006. 10.1021/ol053092b S1523-7060(05)03092-0
Web Release Date: February 14, 2006

Enantioselective Total Synthesis of (-)-Dactylolide

Ignace Louis, Natasha L. Hungerford, Edward J. Humphries, and Malcolm D. McLeod*

School of Chemistry, F11, The University of Sydney, NSW 2006, Australia

m.mcleod@chem.usyd.edu.au

Received December 21, 2005

Abstract:

The enantioselective total synthesis of (-)-dactylolide is reported. The absolute stereochemistry of the tetrahydropyran was established by catalytic asymmetric Jacobsen hetero-Diels-Alder reaction. The remote C19 stereocenter was introduced by a sequence of chelation-controlled Grignard addition and Ireland-Claisen rearrangement.

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