Enantioselective total synthesis of (-)-dactylolide

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

doi:10.1021/ol053092b

Author(s)

Louis, Ignace

L. Hungerford, Natasha

J. Humphries, Edward

D. McLeod, Malcolm

Griffith University Author(s)

Hungerford, Natasha L.

Year published

2006

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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.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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Journal Title

Organic Letters

Volume

Issue

DOI

https://doi.org/10.1021/ol053092b

Subject

Organic Chemical Synthesis

Chemical Sciences

Publication URI

http://hdl.handle.net/10072/28186

Collection

Journal articles