A cobaloxime-mediated synthesis of the ras farnesyl-protein transferase inhibitor chaetomellic acid A

Bruce P. Branchaud; Rachel M. Slade

doi:10.1016/S0040-4039(00)73114-5

A cobaloxime-mediated synthesis of the ras farnesyl-protein transferase inhibitor chaetomellic acid A

Bruce P. Branchaud
, Rachel M. Slade

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

40 Scopus citations

Abstract

A short and efficient synthesis of chaetomellic acid A anhydride (2) is reported utilizing a doubly chemoselective cross coupling of myristyl cobaloxime with citraconic anhydride and diphenyl disulfide as the key step. Sulfide oxidation followed by syn elimination provides 2 in 64% overall yield starting from myristyl bromide. Basic hydrolysis of 2 is known to provide chaetomellic acid A dianion (3), the biologically active form.

Original language	English (US)
Pages (from-to)	4071-4072
Number of pages	2
Journal	Tetrahedron Letters
Volume	35
Issue number	24
DOIs	https://doi.org/10.1016/S0040-4039(00)73114-5
State	Published - Jun 13 1994
Externally published	Yes

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/S0040-4039(00)73114-5

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title = "A cobaloxime-mediated synthesis of the ras farnesyl-protein transferase inhibitor chaetomellic acid A",

abstract = "A short and efficient synthesis of chaetomellic acid A anhydride (2) is reported utilizing a doubly chemoselective cross coupling of myristyl cobaloxime with citraconic anhydride and diphenyl disulfide as the key step. Sulfide oxidation followed by syn elimination provides 2 in 64\% overall yield starting from myristyl bromide. Basic hydrolysis of 2 is known to provide chaetomellic acid A dianion (3), the biologically active form.",

author = "Branchaud, \{Bruce P.\} and Slade, \{Rachel M.\}",

year = "1994",

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doi = "10.1016/S0040-4039(00)73114-5",

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journal = "Tetrahedron Letters",

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AU - Branchaud, Bruce P.

AU - Slade, Rachel M.

PY - 1994/6/13

Y1 - 1994/6/13

N2 - A short and efficient synthesis of chaetomellic acid A anhydride (2) is reported utilizing a doubly chemoselective cross coupling of myristyl cobaloxime with citraconic anhydride and diphenyl disulfide as the key step. Sulfide oxidation followed by syn elimination provides 2 in 64% overall yield starting from myristyl bromide. Basic hydrolysis of 2 is known to provide chaetomellic acid A dianion (3), the biologically active form.

AB - A short and efficient synthesis of chaetomellic acid A anhydride (2) is reported utilizing a doubly chemoselective cross coupling of myristyl cobaloxime with citraconic anhydride and diphenyl disulfide as the key step. Sulfide oxidation followed by syn elimination provides 2 in 64% overall yield starting from myristyl bromide. Basic hydrolysis of 2 is known to provide chaetomellic acid A dianion (3), the biologically active form.

UR - https://www.scopus.com/pages/publications/0028305482

UR - https://www.scopus.com/pages/publications/0028305482#tab=citedBy

U2 - 10.1016/S0040-4039(00)73114-5

DO - 10.1016/S0040-4039(00)73114-5

M3 - Article

AN - SCOPUS:0028305482

SN - 0040-4039

VL - 35

SP - 4071

EP - 4072

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 24

ER -

A cobaloxime-mediated synthesis of the ras farnesyl-protein transferase inhibitor chaetomellic acid A

Abstract

ASJC Scopus subject areas

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