A spirodiepoxide-based strategy to the A-B ring system of pectenotoxin 4

Stephen D. Lotesta; Yongquan Hou; Lawrence J. Williams

doi:10.1021/ol063087n

A spirodiepoxide-based strategy to the A-B ring system of pectenotoxin 4

Stephen D. Lotesta, Yongquan Hou, Lawrence J. Williams

School of Arts and Sciences, Chemistry & Chemical Biology

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

44 Scopus citations

Abstract

(Chemical Equation Presented) A synthesis of a pectenotoxin 4 C1-C15 segment is reported. Suitable C1-C7 and C8-C15 segments were prepared, coupled, converted to I and the C3-hydroxy variant, and then cyclized. Key findings include the stereoselective conversion of the allene to the corresponding spirodiepoxide, oxidative cleavage of the p-methoxybenzyl ether, and cyclization of the spirodiepoxide to spiroketal II.

Original language	English (US)
Pages (from-to)	869-872
Number of pages	4
Journal	Organic letters
Volume	9
Issue number	5
DOIs	https://doi.org/10.1021/ol063087n
State	Published - Mar 1 2007

All Science Journal Classification (ASJC) codes

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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10.1021/ol063087n

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abstract = "(Chemical Equation Presented) A synthesis of a pectenotoxin 4 C1-C15 segment is reported. Suitable C1-C7 and C8-C15 segments were prepared, coupled, converted to I and the C3-hydroxy variant, and then cyclized. Key findings include the stereoselective conversion of the allene to the corresponding spirodiepoxide, oxidative cleavage of the p-methoxybenzyl ether, and cyclization of the spirodiepoxide to spiroketal II.",

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AU - Hou, Yongquan

AU - Williams, Lawrence J.

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Y1 - 2007/3/1

N2 - (Chemical Equation Presented) A synthesis of a pectenotoxin 4 C1-C15 segment is reported. Suitable C1-C7 and C8-C15 segments were prepared, coupled, converted to I and the C3-hydroxy variant, and then cyclized. Key findings include the stereoselective conversion of the allene to the corresponding spirodiepoxide, oxidative cleavage of the p-methoxybenzyl ether, and cyclization of the spirodiepoxide to spiroketal II.

AB - (Chemical Equation Presented) A synthesis of a pectenotoxin 4 C1-C15 segment is reported. Suitable C1-C7 and C8-C15 segments were prepared, coupled, converted to I and the C3-hydroxy variant, and then cyclized. Key findings include the stereoselective conversion of the allene to the corresponding spirodiepoxide, oxidative cleavage of the p-methoxybenzyl ether, and cyclization of the spirodiepoxide to spiroketal II.

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A spirodiepoxide-based strategy to the A-B ring system of pectenotoxin 4

Abstract

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