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Synthesis of the Pluramycins 1: Two Designed Anthrones as Enabling Platforms for Flexible Bis‐C‐Glycosylation
Author(s) -
Kitamura Kei,
Ando Yoshio,
Matsumoto Takashi,
Suzuki Keisuke
Publication year - 2014
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201308016
Subject(s) - stereoselectivity , glycosylation , chemistry , lewis acids and bases , combinatorial chemistry , tricyclic , glycoside , stereochemistry , organic chemistry , catalysis , biochemistry
Two effective tricyclic platforms are reported for the installation of the two constituent sugars, L ‐vancosamine and D ‐angolosamine, in a regio‐ and stereoselective manner for the synthesis of the pluramycin class of bis‐C‐glycoside antitumor antibiotics. Two complementary protocols are now available that differ in the order in which the two sugar moieties are installed. Sc(OTf) 3 was effective as the Lewis acid.