Total synthesis of polycephalin C and determination of the absolute configurations at the 3′′,4′′ ring junction

Deborah A. Longbottom; Angus J. Morrison; Darren J. Dixon; Steven V. Ley

doi:10.1002/1521-3773(20020802)41:15<2786::AID- ANIE2786>3.0.CO;2-Z

Total synthesis of polycephalin C and determination of the absolute configurations at the 3′′,4′′ ring junction

Deborah A. Longbottom, Angus J. Morrison, Darren J. Dixon, Steven V. Ley

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

Abstract

Only through total synthesis could the absolute configuration of the 3′′R,4′′R ring junction of the polyenoltetramic acid polycephalin C (1) be unambiguously established. Key features of the synthesis include a double Swern oxidation, double Stille coupling, and a double Takai olefination.

Original language	English
Pages (from-to)	2786-2790
Number of pages	4
Journal	Angewandte Chemie - International Edition
Volume	41
Issue number	15
DOIs	https://doi.org/10.1002/1521-3773(20020802)41:15<2786::AID- ANIE2786>3.0.CO;2-Z
Publication status	Published - 2 Aug 2002

Keywords

Alkenes
Lactams
Natural products
Total synthesis

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10.1002/1521-3773(20020802)41:15<2786::AID- ANIE2786>3.0.CO;2-Z

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title = "Total synthesis of polycephalin C and determination of the absolute configurations at the 3′′,4′′ ring junction",

abstract = "Only through total synthesis could the absolute configuration of the 3′′R,4′′R ring junction of the polyenoltetramic acid polycephalin C (1) be unambiguously established. Key features of the synthesis include a double Swern oxidation, double Stille coupling, and a double Takai olefination.",

keywords = "Alkenes, Lactams, Natural products, Total synthesis",

author = "Longbottom, {Deborah A.} and Morrison, {Angus J.} and Dixon, {Darren J.} and Ley, {Steven V.}",

year = "2002",

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T1 - Total synthesis of polycephalin C and determination of the absolute configurations at the 3′′,4′′ ring junction

AU - Longbottom, Deborah A.

AU - Morrison, Angus J.

AU - Dixon, Darren J.

AU - Ley, Steven V.

PY - 2002/8/2

Y1 - 2002/8/2

N2 - Only through total synthesis could the absolute configuration of the 3′′R,4′′R ring junction of the polyenoltetramic acid polycephalin C (1) be unambiguously established. Key features of the synthesis include a double Swern oxidation, double Stille coupling, and a double Takai olefination.

AB - Only through total synthesis could the absolute configuration of the 3′′R,4′′R ring junction of the polyenoltetramic acid polycephalin C (1) be unambiguously established. Key features of the synthesis include a double Swern oxidation, double Stille coupling, and a double Takai olefination.

KW - Alkenes

KW - Lactams

KW - Natural products

KW - Total synthesis

U2 - 10.1002/1521-3773(20020802)41:15<2786::AID- ANIE2786>3.0.CO;2-Z

DO - 10.1002/1521-3773(20020802)41:15<2786::AID- ANIE2786>3.0.CO;2-Z

M3 - Article

SN - 1433-7851

VL - 41

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JO - Angewandte Chemie - International Edition

JF - Angewandte Chemie - International Edition

IS - 15

ER -

Total synthesis of polycephalin C and determination of the absolute configurations at the 3′′,4′′ ring junction

Abstract

Keywords

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