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Studies toward the total synthesis of (−)-kampanol A: an efficient construction of the ABCD ring system

Authors
Journal
Tetrahedron Letters
0040-4039
Publisher
Elsevier
Publication Date
Volume
43
Issue
44
Identifiers
DOI: 10.1016/s0040-4039(02)01859-2
Keywords
  • Kampanol A
  • Ras Farnesyltransferase Inhibitor
  • Conjugate Addition
  • Phenylselenium-Mediated Cyclization

Abstract

Abstract The optically active tetracyclic ABCD ring system 2 of (−)-kampanol A ( 1 ), a novel Ras farnesyltransferase inhibitor from a microorganism, was efficiently synthesized starting from the known ketol 4 as a model study. The synthetic method involves conjugate addition reaction of the Grignard reagent of the bromobenzene derivative 14 to the α-methylene ketone 10 to form the coupling product 15 and phenylselenium-mediated cyclization reaction of the phenol derivative 17 to stereoselectively construct the requisite tetracyclic intermediate 18 as the pivotal steps.

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