American Chemical Society
ol053092b_si_001.pdf (1.18 MB)

Enantioselective Total Synthesis of (−)-Dactylolide

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journal contribution
posted on 2006-03-16, 00:00 authored by Ignace Louis, Natasha L. Hungerford, Edward J. Humphries, Malcolm D. McLeod
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.