Enantioselective total synthesis of (-)-dactylolide

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

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Publication date

March 2006

DOI

10.1021/ol053092b

Publisher

American Chemical Society (ACS)

ISSN

1523-7060

Citation count (estimate)

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