Concise stereoselective routes to advanced intermediates related to natural and unnatural pinnaic acid

Matthew W. Carson; Guncheol Kim; Martin F. Hentemann; Dirk Trauner; Samuel J. Danishefsky

doi:10.1002/1521-3773(20011203)40:23<4450::AID-ANIE4450>3.0.CO;2-M

Concise stereoselective routes to advanced intermediates related to natural and unnatural pinnaic acid

Matthew W. Carson, Guncheol Kim, Martin F. Hentemann, Dirk Trauner, Samuel J. Danishefsky

Chemistry

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

Abstract

Important intermediates: In an effort to synthesize and determine the stereo-chemistry of pinnaic acid, C14-epimeric aldehydes 1 and 2 were generated from Meyers' lactam 3. A key step in the parallel syntheses is a highly stereoselective vinylogous Michael cyclization; Boc = tert-butoxy carbonyl, TFA = trifluoro-acetic acid.

Original language	English (US)
Pages (from-to)	4450-4452
Number of pages	3
Journal	Angewandte Chemie - International Edition
Volume	40
Issue number	23
DOIs	https://doi.org/10.1002/1521-3773(20011203)40:23<4450::AID-ANIE4450>3.0.CO;2-M
State	Published - Dec 3 2001

Keywords

Alkaloids
Asymmetric synthesis
Natural products
Total synthesis

ASJC Scopus subject areas

Catalysis
General Chemistry

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10.1002/1521-3773(20011203)40:23<4450::AID-ANIE4450>3.0.CO;2-M

Cite this

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abstract = "Important intermediates: In an effort to synthesize and determine the stereo-chemistry of pinnaic acid, C14-epimeric aldehydes 1 and 2 were generated from Meyers' lactam 3. A key step in the parallel syntheses is a highly stereoselective vinylogous Michael cyclization; Boc = tert-butoxy carbonyl, TFA = trifluoro-acetic acid.",

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AU - Carson, Matthew W.

AU - Kim, Guncheol

AU - Hentemann, Martin F.

AU - Trauner, Dirk

AU - Danishefsky, Samuel J.

PY - 2001/12/3

Y1 - 2001/12/3

N2 - Important intermediates: In an effort to synthesize and determine the stereo-chemistry of pinnaic acid, C14-epimeric aldehydes 1 and 2 were generated from Meyers' lactam 3. A key step in the parallel syntheses is a highly stereoselective vinylogous Michael cyclization; Boc = tert-butoxy carbonyl, TFA = trifluoro-acetic acid.

AB - Important intermediates: In an effort to synthesize and determine the stereo-chemistry of pinnaic acid, C14-epimeric aldehydes 1 and 2 were generated from Meyers' lactam 3. A key step in the parallel syntheses is a highly stereoselective vinylogous Michael cyclization; Boc = tert-butoxy carbonyl, TFA = trifluoro-acetic acid.

KW - Alkaloids

KW - Asymmetric synthesis

KW - Natural products

KW - Total synthesis

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Concise stereoselective routes to advanced intermediates related to natural and unnatural pinnaic acid

Abstract

Keywords

ASJC Scopus subject areas

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