A COBALOXIME-MEDIATED SYNTHESIS OF THE RAS FARNESYL-PROTEIN TRANSFERASE INHIBITOR CHAETOMELLIC ACID-A

Authors
BRANCHAUD BP SLADE RM
Citation
Bp. Branchaud et Rm. Slade, A COBALOXIME-MEDIATED SYNTHESIS OF THE RAS FARNESYL-PROTEIN TRANSFERASE INHIBITOR CHAETOMELLIC ACID-A, Tetrahedron letters, 35(24), 1994, pp. 4071-4072
Citations number
6
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron letters → ACNP
ISSN journal
00404039
Volume
35
Issue
24
Year of publication
1994
Pages
4071 - 4072
Database
ISI
SICI code
0040-4039(1994)35:24<4071:ACSOTR>2.0.ZU;2-W
Abstract
A short and efficient synthesis of chaetometlic acid A anhydride (2) i s reported utilizing a doubly chemoselective cross coupling of myristy l cobaloxime with citraconic anhydride and diphenyl disulfide as the k ey step. Sulfide oxidation followed by syn elimination provides 2 in 6 4% overall yield starting from myristyl bromide. Basic hydrolysis of 2 is known to provide chaetomellic acid A dianion (3), the biologically active form.