Investigations into a Biomimetic Approach toward CP-225,917 and CP-263,114

• Published in: Journal of organic chemistry Vol. 65; no. 2; pp. 337 - 342
• Main Authors: Sulikowski, Gary A, Agnelli, Fabio, Corbett, R. Michael
• Format: Journal Article
• Language: English
• Published: WASHINGTON American Chemical Society 28.01.2000; Amer Chemical Soc
• Subjects: Chemistry; Chemistry, Organic; Enzyme Inhibitors - chemistry; Enzyme Inhibitors - metabolism; Farnesyl-Diphosphate Farnesyltransferase - antagonists & inhibitors; Maleic Anhydrides - chemistry; Maleic Anhydrides - metabolism; Molecular Mimicry; Molecular Structure; Physical Sciences; Science & Technology; Spectrum Analysis; CORE; UNIDENTIFIED FUNGUS; RAS FARNESYLATION INHIBITORS
• ISSN: 0022-3263; 1520-6904
• DOI: 10.1021/jo9911286

A biosynthesis of the structurally complex nonadride CP-225,917 (1) is outlined. A key step in this proposal is the dimerization of a C16 anhydride derived from the condensation of lauric acid and oxaloacetic acid. An important element of this step is a templating effect imposed by two thioester linkages, reminiscent of a polyketide or fatty acid synthase pathway. On the basis of this principle, the dimerization of two C11 anhydrides, templated by a 1,n-diol tether, leading to the core structure of CP-225,917 and CP-263,114 was investigated.