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A hetero-Diels-Alder approach to complex pyrones: an improved synthesis of the spongistatin AB spiroketal.

ABSTRACT: The conversion of a substituted dioxinone to a pyrone was used in an improved synthesis of the AB spiroketal subunit of the spongistatins. This transformation occurred via a hetero-Diels-Alder reaction of an acyl ketene with butyl vinyl ether. A double diastereoselective Mukaiyama aldol reaction is used to provide the hetero-Diels-Alder precursor.

SUBMITTER: Crimmins MT

PROVIDER: S-EPMC2546580 | biostudies-literature | 2006 Mar

REPOSITORIES: biostudies-literature

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A hetero-Diels-Alder approach to complex pyrones: an improved synthesis of the spongistatin AB spiroketal.

Crimmins Michael T MT Smith Aaron C AC

Organic letters 20060301 5

The conversion of a substituted dioxinone to a pyrone was used in an improved synthesis of the AB spiroketal subunit of the spongistatins. This transformation occurred via a hetero-Diels-Alder reaction of an acyl ketene with butyl vinyl ether. A double diastereoselective Mukaiyama aldol reaction is used to provide the hetero-Diels-Alder precursor. ...[more]

PMID: 16494495

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