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

• Published in: Tetrahedron letters Vol. 43; no. 44; pp. 7937 - 7940
• Main Authors: Iwasaki, Katsuhiko, Nakatani, Mari, Inoue, Munenori, Katoh, Tadashi
• Format: Journal Article
• Language: English
• Published: OXFORD Elsevier Ltd 28.10.2002; Elsevier
• Subjects: Chemistry; Chemistry, Organic; conjugate addition; kampanol A; phenylselenium-mediated cyclization; Physical Sciences; Ras farnesyltransferase inhibitor; Science & Technology; Ras farnesyltransferase inhibitor; conjugate addition; kampanol A; phenylselenium-mediated cyclization; OXIDATION; DESS-MARTIN PERIODINANE; ENANTIOSPECIFIC SYNTHESIS; RAS FARNESYLTRANSFERASE; SECONDARY ALCOHOLS; HONGOQUERCIN; ABSOLUTE-CONFIGURATION; FUNGAL METABOLITE; INHIBITORS

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...