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

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...

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Bibliographic Details
Published inTetrahedron letters Vol. 43; no. 44; pp. 7937 - 7940
Main Authors Iwasaki, Katsuhiko, Nakatani, Mari, Inoue, Munenori, Katoh, Tadashi
Format Journal Article
LanguageEnglish
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
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Summary: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. Graphic
ISSN:0040-4039
1873-3581
DOI:10.1016/S0040-4039(02)01859-2