A formal synthesis of psymberin

Ning Shangguan; Sezgin Kiren; Lawrence J. Williams

doi:10.1021/ol063143k

A formal synthesis of psymberin

Ning Shangguan, Sezgin Kiren, Lawrence J. Williams

School of Arts and Sciences, Chemistry & Chemical Biology

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

81 Scopus citations

Abstract

(Chemical Equation Presented) A formal synthesis of psymberin (irciniastatin A) is presented. Notable features of the synthesis include the chemo-, regio-, and stereoselective oxidation of a 1,3-disubstituted allene, a configuration-dependent spirodiepoxide opening, the efficient syntheses of functionalized trans-2,6-disubstituted pyrans, and the union of a highly functionalized aldehyde with a pentasubstituted aryl homoenolate to give a dihydroisocumarin.

Original language	English (US)
Pages (from-to)	1093-1096
Number of pages	4
Journal	Organic letters
Volume	9
Issue number	6
DOIs	https://doi.org/10.1021/ol063143k
State	Published - Mar 15 2007

All Science Journal Classification (ASJC) codes

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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10.1021/ol063143k

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abstract = "(Chemical Equation Presented) A formal synthesis of psymberin (irciniastatin A) is presented. Notable features of the synthesis include the chemo-, regio-, and stereoselective oxidation of a 1,3-disubstituted allene, a configuration-dependent spirodiepoxide opening, the efficient syntheses of functionalized trans-2,6-disubstituted pyrans, and the union of a highly functionalized aldehyde with a pentasubstituted aryl homoenolate to give a dihydroisocumarin.",

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year = "2007",

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AU - Shangguan, Ning

AU - Kiren, Sezgin

AU - Williams, Lawrence J.

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Y1 - 2007/3/15

N2 - (Chemical Equation Presented) A formal synthesis of psymberin (irciniastatin A) is presented. Notable features of the synthesis include the chemo-, regio-, and stereoselective oxidation of a 1,3-disubstituted allene, a configuration-dependent spirodiepoxide opening, the efficient syntheses of functionalized trans-2,6-disubstituted pyrans, and the union of a highly functionalized aldehyde with a pentasubstituted aryl homoenolate to give a dihydroisocumarin.

AB - (Chemical Equation Presented) A formal synthesis of psymberin (irciniastatin A) is presented. Notable features of the synthesis include the chemo-, regio-, and stereoselective oxidation of a 1,3-disubstituted allene, a configuration-dependent spirodiepoxide opening, the efficient syntheses of functionalized trans-2,6-disubstituted pyrans, and the union of a highly functionalized aldehyde with a pentasubstituted aryl homoenolate to give a dihydroisocumarin.

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A formal synthesis of psymberin

Abstract

All Science Journal Classification (ASJC) codes

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