Stereoselection in the Prins-pinacol synthesis of 2,2-disubstituted 4-acyltetrahydrofurans. Enantioselective synthesis of (-)-citreoviral

Naoyuki Hanaki; J. T. Link; David W.C. MacMillan; Larry E. Overman; William G. Trankle; Julie A. Wurster

doi:10.1021/ol991315q

Stereoselection in the Prins-pinacol synthesis of 2,2-disubstituted 4-acyltetrahydrofurans. Enantioselective synthesis of (-)-citreoviral

Naoyuki Hanaki, J. T. Link, David W.C. MacMillan, Larry E. Overman, William G. Trankle, Julie A. Wurster

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

58 Scopus citations

Abstract

(matrix presented) The condensation of allylic diols with unsymmetrical ketones proceeds with high stereoselection to form 2,2-disubstituted 4-acyltetrahydrofurans when the α-substituents of the ketone differ substantially in size. A Prins-pinacol condensation of this type is the central strategic step in an enantioselective synthesis of (-)-citreoviral.

Original language	English (US)
Pages (from-to)	223-226
Number of pages	4
Journal	Organic letters
Volume	2
Issue number	2
DOIs	https://doi.org/10.1021/ol991315q
State	Published - Jan 27 2000
Externally published	Yes

All Science Journal Classification (ASJC) codes

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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10.1021/ol991315q

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title = "Stereoselection in the Prins-pinacol synthesis of 2,2-disubstituted 4-acyltetrahydrofurans. Enantioselective synthesis of (-)-citreoviral",

abstract = "(matrix presented) The condensation of allylic diols with unsymmetrical ketones proceeds with high stereoselection to form 2,2-disubstituted 4-acyltetrahydrofurans when the α-substituents of the ketone differ substantially in size. A Prins-pinacol condensation of this type is the central strategic step in an enantioselective synthesis of (-)-citreoviral.",

author = "Naoyuki Hanaki and Link, {J. T.} and MacMillan, {David W.C.} and Overman, {Larry E.} and Trankle, {William G.} and Wurster, {Julie A.}",

year = "2000",

month = jan,

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doi = "10.1021/ol991315q",

language = "English (US)",

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journal = "Organic letters",

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AU - Hanaki, Naoyuki

AU - Link, J. T.

AU - MacMillan, David W.C.

AU - Overman, Larry E.

AU - Trankle, William G.

AU - Wurster, Julie A.

PY - 2000/1/27

Y1 - 2000/1/27

N2 - (matrix presented) The condensation of allylic diols with unsymmetrical ketones proceeds with high stereoselection to form 2,2-disubstituted 4-acyltetrahydrofurans when the α-substituents of the ketone differ substantially in size. A Prins-pinacol condensation of this type is the central strategic step in an enantioselective synthesis of (-)-citreoviral.

AB - (matrix presented) The condensation of allylic diols with unsymmetrical ketones proceeds with high stereoselection to form 2,2-disubstituted 4-acyltetrahydrofurans when the α-substituents of the ketone differ substantially in size. A Prins-pinacol condensation of this type is the central strategic step in an enantioselective synthesis of (-)-citreoviral.

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ER -

Stereoselection in the Prins-pinacol synthesis of 2,2-disubstituted 4-acyltetrahydrofurans. Enantioselective synthesis of (-)-citreoviral

Abstract

All Science Journal Classification (ASJC) codes

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