Application of a domino intramolecular enyne metathesis/cross metathesis reaction to the total synthesis of (+)-8-epi-xanthatin

David A. Kummer; Jehrod B. Brenneman; Stephen F. Martin

doi:10.1021/ol051711a

Application of a domino intramolecular enyne metathesis/cross metathesis reaction to the total synthesis of (+)-8-epi-xanthatin

David A. Kummer
, Jehrod B. Brenneman
, Stephen F. Martin

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

87 Scopus citations

Abstract

(Chemical Equation Presented) The first total synthesis of the novel sesquiterpene lactone (+)-8-epi-xanthatin (1) has been achieved starting from the commercially available ester 8. The synthesis features an asymmetric aldol reaction and palladium-catalyzed carbonylation/lactonization sequence leading to 4 and a domino ring-closing enyne metathesis/cross metathesis reaction to afford 1.

Original language	English (US)
Pages (from-to)	4621-4623
Number of pages	3
Journal	Organic Letters
Volume	7
Issue number	21
DOIs	https://doi.org/10.1021/ol051711a
State	Published - Oct 13 2005
Externally published	Yes

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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10.1021/ol051711a

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abstract = "(Chemical Equation Presented) The first total synthesis of the novel sesquiterpene lactone (+)-8-epi-xanthatin (1) has been achieved starting from the commercially available ester 8. The synthesis features an asymmetric aldol reaction and palladium-catalyzed carbonylation/lactonization sequence leading to 4 and a domino ring-closing enyne metathesis/cross metathesis reaction to afford 1.",

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AU - Kummer, David A.

AU - Brenneman, Jehrod B.

AU - Martin, Stephen F.

PY - 2005/10/13

Y1 - 2005/10/13

N2 - (Chemical Equation Presented) The first total synthesis of the novel sesquiterpene lactone (+)-8-epi-xanthatin (1) has been achieved starting from the commercially available ester 8. The synthesis features an asymmetric aldol reaction and palladium-catalyzed carbonylation/lactonization sequence leading to 4 and a domino ring-closing enyne metathesis/cross metathesis reaction to afford 1.

AB - (Chemical Equation Presented) The first total synthesis of the novel sesquiterpene lactone (+)-8-epi-xanthatin (1) has been achieved starting from the commercially available ester 8. The synthesis features an asymmetric aldol reaction and palladium-catalyzed carbonylation/lactonization sequence leading to 4 and a domino ring-closing enyne metathesis/cross metathesis reaction to afford 1.

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U2 - 10.1021/ol051711a

DO - 10.1021/ol051711a

M3 - Article

C2 - 16209494

AN - SCOPUS:27144526502

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JO - Organic Letters

JF - Organic Letters

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Application of a domino intramolecular enyne metathesis/cross metathesis reaction to the total synthesis of (+)-8-epi-xanthatin

Abstract

ASJC Scopus subject areas

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