Total synthesis of the polyenoyltetramic acid polycephalin C

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

doi:10.1016/S0040-4020(03)00816-0

Total synthesis of the polyenoyltetramic acid polycephalin C

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

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

Abstract

The total synthesis of the polyenoyltetramic acid polycephalin C is described. Key steps of the synthesis include a double Swern oxidation, double Takai reaction and a double Stille reaction. In addition, the absolute stereochemistry of the ring junction has been determined by synthesis of both isomers and comparison of their CD spectra with natural polycephalin C. © 2003 Elsevier Ltd. All rights reserved.

Original language	English
Pages (from-to)	6955-6966
Number of pages	11
Journal	Tetrahedron
Volume	59
Issue number	35
DOIs	https://doi.org/10.1016/S0040-4020(03)00816-0
Publication status	Published - 25 Aug 2003

Keywords

Lactams
Natural product synthesis
Swern oxidation
Takai reaction
Tetramic acids

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10.1016/S0040-4020(03)00816-0

Cite this

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title = "Total synthesis of the polyenoyltetramic acid polycephalin C",

abstract = "The total synthesis of the polyenoyltetramic acid polycephalin C is described. Key steps of the synthesis include a double Swern oxidation, double Takai reaction and a double Stille reaction. In addition, the absolute stereochemistry of the ring junction has been determined by synthesis of both isomers and comparison of their CD spectra with natural polycephalin C. {\textcopyright} 2003 Elsevier Ltd. All rights reserved.",

keywords = "Lactams, Natural product synthesis, Swern oxidation, Takai reaction, Tetramic acids",

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

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AU - Longbottom, Deborah A.

AU - Morrison, Angus J.

AU - Dixon, Darren J.

AU - Ley, Steven V.

PY - 2003/8/25

Y1 - 2003/8/25

N2 - The total synthesis of the polyenoyltetramic acid polycephalin C is described. Key steps of the synthesis include a double Swern oxidation, double Takai reaction and a double Stille reaction. In addition, the absolute stereochemistry of the ring junction has been determined by synthesis of both isomers and comparison of their CD spectra with natural polycephalin C. © 2003 Elsevier Ltd. All rights reserved.

AB - The total synthesis of the polyenoyltetramic acid polycephalin C is described. Key steps of the synthesis include a double Swern oxidation, double Takai reaction and a double Stille reaction. In addition, the absolute stereochemistry of the ring junction has been determined by synthesis of both isomers and comparison of their CD spectra with natural polycephalin C. © 2003 Elsevier Ltd. All rights reserved.

KW - Lactams

KW - Natural product synthesis

KW - Swern oxidation

KW - Takai reaction

KW - Tetramic acids

U2 - 10.1016/S0040-4020(03)00816-0

DO - 10.1016/S0040-4020(03)00816-0

M3 - Article

SN - 0040-4020

VL - 59

SP - 6955

EP - 6966

JO - Tetrahedron

JF - Tetrahedron

IS - 35

ER -

Total synthesis of the polyenoyltetramic acid polycephalin C

Abstract

Keywords

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