Concise total synthesis of (-)-frondosin B using a novel palladium-catalyzed cyclization

Chambers C. Hughes; Dirk Trauner

doi:10.1002/1521-3773(20020503)41:9<1569::AID-ANIE1569>3.0.CO;2-8

Concise total synthesis of (-)-frondosin B using a novel palladium-catalyzed cyclization

Chambers C. Hughes, Dirk Trauner

Chemistry

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

Abstract

Sidestepping stereochemical inversion: In an expedient, asymmetric total synthesis of (-)-frondosin B a novel palladium-catalyzed cyclization establishes the tetracyclic skeleton (see scheme). The absolute stereochemistry of naturally occurring marine metabolite (+)-frondosin B, an interleukin-8 inhibitor, has been reassigned. Tf = trifluoromethanesulfonyl.

Original language	English (US)
Pages (from-to)	1569-1572
Number of pages	4
Journal	Angewandte Chemie - International Edition
Volume	41
Issue number	9
DOIs	https://doi.org/10.1002/1521-3773(20020503)41:9<1569::AID-ANIE1569>3.0.CO;2-8
State	Published - May 3 2002

Keywords

Cyclization
Natural products
Palladium
Polycycles
Total synthesis

ASJC Scopus subject areas

Catalysis
General Chemistry

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10.1002/1521-3773(20020503)41:9<1569::AID-ANIE1569>3.0.CO;2-8

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N2 - Sidestepping stereochemical inversion: In an expedient, asymmetric total synthesis of (-)-frondosin B a novel palladium-catalyzed cyclization establishes the tetracyclic skeleton (see scheme). The absolute stereochemistry of naturally occurring marine metabolite (+)-frondosin B, an interleukin-8 inhibitor, has been reassigned. Tf = trifluoromethanesulfonyl.

AB - Sidestepping stereochemical inversion: In an expedient, asymmetric total synthesis of (-)-frondosin B a novel palladium-catalyzed cyclization establishes the tetracyclic skeleton (see scheme). The absolute stereochemistry of naturally occurring marine metabolite (+)-frondosin B, an interleukin-8 inhibitor, has been reassigned. Tf = trifluoromethanesulfonyl.

KW - Cyclization

KW - Natural products

KW - Palladium

KW - Polycycles

KW - Total synthesis

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Concise total synthesis of (-)-frondosin B using a novel palladium-catalyzed cyclization

Abstract

Keywords

ASJC Scopus subject areas

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