Total syntheses of (±)-cis-trikentrin A and (±)-cis- trikentrin B via electrocyclic ring closures of 2,3-divinylpyrrolines

Raymond J. Huntley; Raymond L. Funk

doi:10.1021/ol061259a

Total syntheses of (±)-cis-trikentrin A and (±)-cis- trikentrin B via electrocyclic ring closures of 2,3-divinylpyrrolines

Raymond J. Huntley, Raymond L. Funk

Chemistry

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

44 Scopus citations

Abstract

A convergent and versatile strategy for the diastereoselective syntheses of (±)-cis-trikentrin A and B in 10 and 12 steps, respectively, from commercially available N-BOC-2-pyrrolidinone is described. The key step in each of the total syntheses is the construction of the central benzene ring via a facile 6π-electrocyclic ring closure of an appropriately substituted 2,3-divinylpyrroline, in turn, readily available by a Stille coupling reaction.

Original language	English (US)
Pages (from-to)	3403-3406
Number of pages	4
Journal	Organic Letters
Volume	8
Issue number	15
DOIs	https://doi.org/10.1021/ol061259a
State	Published - Jul 20 2006

All Science Journal Classification (ASJC) codes

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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10.1021/ol061259a

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abstract = "A convergent and versatile strategy for the diastereoselective syntheses of (±)-cis-trikentrin A and B in 10 and 12 steps, respectively, from commercially available N-BOC-2-pyrrolidinone is described. The key step in each of the total syntheses is the construction of the central benzene ring via a facile 6π-electrocyclic ring closure of an appropriately substituted 2,3-divinylpyrroline, in turn, readily available by a Stille coupling reaction.",

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PY - 2006/7/20

Y1 - 2006/7/20

N2 - A convergent and versatile strategy for the diastereoselective syntheses of (±)-cis-trikentrin A and B in 10 and 12 steps, respectively, from commercially available N-BOC-2-pyrrolidinone is described. The key step in each of the total syntheses is the construction of the central benzene ring via a facile 6π-electrocyclic ring closure of an appropriately substituted 2,3-divinylpyrroline, in turn, readily available by a Stille coupling reaction.

AB - A convergent and versatile strategy for the diastereoselective syntheses of (±)-cis-trikentrin A and B in 10 and 12 steps, respectively, from commercially available N-BOC-2-pyrrolidinone is described. The key step in each of the total syntheses is the construction of the central benzene ring via a facile 6π-electrocyclic ring closure of an appropriately substituted 2,3-divinylpyrroline, in turn, readily available by a Stille coupling reaction.

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Total syntheses of (±)-cis-trikentrin A and (±)-cis- trikentrin B via electrocyclic ring closures of 2,3-divinylpyrrolines

Abstract

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