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Synthesis of the Pluramycins 2: Total Synthesis and Structure Assignment of Saptomycin B
Author(s) -
Kitamura Kei,
Maezawa Yoshihiko,
Ando Yoshio,
Kusumi Takenori,
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.201308017
Subject(s) - total synthesis , regioselectivity , aldol reaction , chemistry , stereochemistry , yield (engineering) , tricyclic , combinatorial chemistry , convergent synthesis , organic chemistry , catalysis , materials science , metallurgy
A concise, highly convergent total synthesis of saptomycin B, a member of the pluramycin class of antitumor antibiotics, is reported. The target compound was assembled from four building blocks (a tricyclic platform, two sugars, and an alkynal) in 15% yield through 10 synthetic operations. The key steps included the regioselective installation of two amino sugars ( L ‐vancosamine and D ‐angolosamine) on the tricycle and the efficient construction of the tetracyclic skeleton by an aldol reaction followed by formation of the pyranone. The unknown configuration at C14 was assigned as R .