Cross coupling of alkyl cobaloximes with maleic anhydrides. Basic studies and applications to the synthesis of chaetomellic acid A anhydride and C-glycosyl maleic anhydrides

Rachel M. Slade, Bruce Branchaud

Research output: Contribution to journalArticle

21 Citations (Scopus)

Abstract

Photochemical cross coupling of alkyl cobaloximes with maleic anhydrides and PhSSPh led to addition of an alkyl moiety and an SPh moiety across the alkene. Oxidation of the sulfide to a sulfoxide followed by elimination of phenyl sulfenic acid provided substituted maleic anhydrides. Alkyl cobaloximes could also be coupled with maleic anhydrides in the absence of PhSSPh to provide substituted maleic anhydrides directly. These methods are applied to a short and efficient synthesis of the anhydride of the Ras farnesyl protein transferase inhibitor chaetomellic acid A and in preparations of C-glycosyl maleic anhydrides, in which the carbohydrate anomeric carbon is directly attached to a maleic anhydride alkene carbon, in modest yields (19-46%).

Original languageEnglish (US)
Pages (from-to)3544-3549
Number of pages6
JournalJournal of Organic Chemistry
Volume63
Issue number11
DOIs
StatePublished - May 29 1998
Externally publishedYes

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Maleic Anhydrides
Anhydrides
sulfoxide
Alkenes
Sulfenic Acids
Carbon
Sulfides
Transferases
cobaloxime
chaetomellic acid A
Carbohydrates
Oxidation

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

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title = "Cross coupling of alkyl cobaloximes with maleic anhydrides. Basic studies and applications to the synthesis of chaetomellic acid A anhydride and C-glycosyl maleic anhydrides",
abstract = "Photochemical cross coupling of alkyl cobaloximes with maleic anhydrides and PhSSPh led to addition of an alkyl moiety and an SPh moiety across the alkene. Oxidation of the sulfide to a sulfoxide followed by elimination of phenyl sulfenic acid provided substituted maleic anhydrides. Alkyl cobaloximes could also be coupled with maleic anhydrides in the absence of PhSSPh to provide substituted maleic anhydrides directly. These methods are applied to a short and efficient synthesis of the anhydride of the Ras farnesyl protein transferase inhibitor chaetomellic acid A and in preparations of C-glycosyl maleic anhydrides, in which the carbohydrate anomeric carbon is directly attached to a maleic anhydride alkene carbon, in modest yields (19-46{\%}).",
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T1 - Cross coupling of alkyl cobaloximes with maleic anhydrides. Basic studies and applications to the synthesis of chaetomellic acid A anhydride and C-glycosyl maleic anhydrides

AU - Slade, Rachel M.

AU - Branchaud, Bruce

PY - 1998/5/29

Y1 - 1998/5/29

N2 - Photochemical cross coupling of alkyl cobaloximes with maleic anhydrides and PhSSPh led to addition of an alkyl moiety and an SPh moiety across the alkene. Oxidation of the sulfide to a sulfoxide followed by elimination of phenyl sulfenic acid provided substituted maleic anhydrides. Alkyl cobaloximes could also be coupled with maleic anhydrides in the absence of PhSSPh to provide substituted maleic anhydrides directly. These methods are applied to a short and efficient synthesis of the anhydride of the Ras farnesyl protein transferase inhibitor chaetomellic acid A and in preparations of C-glycosyl maleic anhydrides, in which the carbohydrate anomeric carbon is directly attached to a maleic anhydride alkene carbon, in modest yields (19-46%).

AB - Photochemical cross coupling of alkyl cobaloximes with maleic anhydrides and PhSSPh led to addition of an alkyl moiety and an SPh moiety across the alkene. Oxidation of the sulfide to a sulfoxide followed by elimination of phenyl sulfenic acid provided substituted maleic anhydrides. Alkyl cobaloximes could also be coupled with maleic anhydrides in the absence of PhSSPh to provide substituted maleic anhydrides directly. These methods are applied to a short and efficient synthesis of the anhydride of the Ras farnesyl protein transferase inhibitor chaetomellic acid A and in preparations of C-glycosyl maleic anhydrides, in which the carbohydrate anomeric carbon is directly attached to a maleic anhydride alkene carbon, in modest yields (19-46%).

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