Diastereodivergent synthesis of the C8–C18 precursor and C1′–C11′ subunit of pamamycin 607 induced by a chiral sulfoxide group

A key step in obtaining the C8–C18 and C1′–C11′ fragments of pamamycin 607, which differ by the syn- and anti-configuration of one chiral center α to the tetrahydrofuran ring, was the chelation controlled E–Z-isomerization of the substituted vinyl tetrahydrofuran intermediate 3a which has so far bee...

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Bibliographic Details
Published inTetrahedron letters Vol. 41; no. 15; pp. 2737 - 2740
Main Authors Solladié, Guy, Salom-Roig, Xavier J, Hanquet, Gilles
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier Ltd 01.04.2000
Elsevier
Subjects
Chemical Sciences
Chemistry
Chemistry, Organic
Organic chemistry
Physical Sciences
Science & Technology
(+)-NONACTIC ACID
ANTIBIOTICS
REDUCTION
STREPTOMYCES-ALBONIGER
SUBSTANCE
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Summary:A key step in obtaining the C8–C18 and C1′–C11′ fragments of pamamycin 607, which differ by the syn- and anti-configuration of one chiral center α to the tetrahydrofuran ring, was the chelation controlled E–Z-isomerization of the substituted vinyl tetrahydrofuran intermediate 3a which has so far been obtained only in the more stable E-configuration.
ISSN:0040-4039
1873-3581
DOI:10.1016/S0040-4039(00)00251-3