Total synthesis of (+)-tautomycin

Tautomycin molecule was disconnected into 3 retrosynthetic segments, A, B and C, each of which was synthesized in optically active form. First coupling between Segments B and C was achieved between an epoxide and a sulfone carbanion in the presence of BF 3·OEt 2. This product (Segment B/C) and Segme...

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Bibliographic Details
Published inTetrahedron letters Vol. 36; no. 39; pp. 7101 - 7104
Main Authors Ichikawa, Yoshiyasu, Tsuboi, Katsunori, Jiang, Yimin, Naganawa, Atsushi, Isobe, Minoru
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier Ltd 25.09.1995
Elsevier
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
OXIDATION
REAGENTS
NATURAL-PRODUCTS
TAUTOMYCIN
EFFICIENT MACROLACTONIZATION
CHIRAL SYNTHESIS
ERYTHRONOLIDE
DERIVATIVES
ANHYDRIDE
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Summary:Tautomycin molecule was disconnected into 3 retrosynthetic segments, A, B and C, each of which was synthesized in optically active form. First coupling between Segments B and C was achieved between an epoxide and a sulfone carbanion in the presence of BF 3·OEt 2. This product (Segment B/C) and Segment A were further coupled by Yamaguchi esterification method. Final transformation of the furan ring into the maleic anhydride and removal of the protecting groups completed the total synthesis of (+)-tautomycin.
ISSN:0040-4039
1873-3581
DOI:10.1016/0040-4039(95)01436-L