Spirodiepoxide strategy to the C ring of pectenotoxin 4: Synthesis of the C1-C19 sector

Sipak Joyasawal; Stephen D. Lotesta; N. G. Akhmedov; Lawrence J. Williams

doi:10.1021/ol902984e

Spirodiepoxide strategy to the C ring of pectenotoxin 4: Synthesis of the C1-C19 sector

Sipak Joyasawal, Stephen D. Lotesta, N. G. Akhmedov, Lawrence J. Williams

School of Arts and Sciences, Chemistry & Chemical Biology

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

30 Scopus citations

Abstract

(Chemical Equetion Presentation) The synthesis of a C1-C19 precursor to pectenotoxin 4 is presented. The strategy employed the functionalized aliene shown. Key features include: olefin metathesis of two simple fragments to prepare the left portion of the allene-precursor, diastereoselective propargylation of an epoxy aldehyde to form the right portion, use of the DMDO-stable m-fluorobenzyl ether, and an aliene spirodiepoxidation/C-ring formation cascade.

Original language	English (US)
Pages (from-to)	988-991
Number of pages	4
Journal	Organic letters
Volume	12
Issue number	5
DOIs	https://doi.org/10.1021/ol902984e
State	Published - Mar 5 2010

All Science Journal Classification (ASJC) codes

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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10.1021/ol902984e

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title = "Spirodiepoxide strategy to the C ring of pectenotoxin 4: Synthesis of the C1-C19 sector",

abstract = "(Chemical Equetion Presentation) The synthesis of a C1-C19 precursor to pectenotoxin 4 is presented. The strategy employed the functionalized aliene shown. Key features include: olefin metathesis of two simple fragments to prepare the left portion of the allene-precursor, diastereoselective propargylation of an epoxy aldehyde to form the right portion, use of the DMDO-stable m-fluorobenzyl ether, and an aliene spirodiepoxidation/C-ring formation cascade.",

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AU - Lotesta, Stephen D.

AU - Akhmedov, N. G.

AU - Williams, Lawrence J.

PY - 2010/3/5

Y1 - 2010/3/5

N2 - (Chemical Equetion Presentation) The synthesis of a C1-C19 precursor to pectenotoxin 4 is presented. The strategy employed the functionalized aliene shown. Key features include: olefin metathesis of two simple fragments to prepare the left portion of the allene-precursor, diastereoselective propargylation of an epoxy aldehyde to form the right portion, use of the DMDO-stable m-fluorobenzyl ether, and an aliene spirodiepoxidation/C-ring formation cascade.

AB - (Chemical Equetion Presentation) The synthesis of a C1-C19 precursor to pectenotoxin 4 is presented. The strategy employed the functionalized aliene shown. Key features include: olefin metathesis of two simple fragments to prepare the left portion of the allene-precursor, diastereoselective propargylation of an epoxy aldehyde to form the right portion, use of the DMDO-stable m-fluorobenzyl ether, and an aliene spirodiepoxidation/C-ring formation cascade.

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Spirodiepoxide strategy to the C ring of pectenotoxin 4: Synthesis of the C1-C19 sector

Abstract

All Science Journal Classification (ASJC) codes

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