IMDA-radical cyclization approach to (+)-himbacine

Leon S.M. Wong; Michael S. Sherburn

doi:10.1021/ol0353058

IMDA-radical cyclization approach to (+)-himbacine

Leon S.M. Wong, Michael S. Sherburn

Research output: Contribution to journal › Article › peer-review

44 Citations (Scopus)

Abstract

(Equation presented) A formal total synthesis of the selective muscarinic receptor antagonist himbacine is presented. Key C-C bond-forming steps include an intramolecular Diels-Alder reaction, Stille coupling reactions, and a 6-exo-trig acyl radical cyclization to a conjugated enyne. An unexpected secondary alcohol to chloride conversion is witnessed during attempted thionocarbonate formation.

Original language	English
Pages (from-to)	3603-3606
Number of pages	4
Journal	Organic Letters
Volume	5
Issue number	20
DOIs	https://doi.org/10.1021/ol0353058
Publication status	Published - 2 Oct 2003

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10.1021/ol0353058

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title = "IMDA-radical cyclization approach to (+)-himbacine",

abstract = "(Equation presented) A formal total synthesis of the selective muscarinic receptor antagonist himbacine is presented. Key C-C bond-forming steps include an intramolecular Diels-Alder reaction, Stille coupling reactions, and a 6-exo-trig acyl radical cyclization to a conjugated enyne. An unexpected secondary alcohol to chloride conversion is witnessed during attempted thionocarbonate formation.",

author = "Wong, \{Leon S.M.\} and Sherburn, \{Michael S.\}",

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AU - Sherburn, Michael S.

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N2 - (Equation presented) A formal total synthesis of the selective muscarinic receptor antagonist himbacine is presented. Key C-C bond-forming steps include an intramolecular Diels-Alder reaction, Stille coupling reactions, and a 6-exo-trig acyl radical cyclization to a conjugated enyne. An unexpected secondary alcohol to chloride conversion is witnessed during attempted thionocarbonate formation.

AB - (Equation presented) A formal total synthesis of the selective muscarinic receptor antagonist himbacine is presented. Key C-C bond-forming steps include an intramolecular Diels-Alder reaction, Stille coupling reactions, and a 6-exo-trig acyl radical cyclization to a conjugated enyne. An unexpected secondary alcohol to chloride conversion is witnessed during attempted thionocarbonate formation.

UR - https://www.scopus.com/pages/publications/0142011144

U2 - 10.1021/ol0353058

DO - 10.1021/ol0353058

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SP - 3603

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JO - Organic Letters

JF - Organic Letters

IS - 20

ER -

IMDA-radical cyclization approach to (+)-himbacine

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