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Asymmetric Synthesis of the C(33) – C(37) Fragment of Amphotericin B
Author(s) -
Tholander Joakim,
Carreira Erick M.
Publication year - 2001
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/1522-2675(20010321)84:3<613::aid-hlca613>3.0.co;2-4
Subject(s) - chemistry , aldehyde , yield (engineering) , stereochemistry , enantioselective synthesis , derivative (finance) , fragment (logic) , amphotericin b , stereocenter , combinatorial chemistry , catalysis , organic chemistry , antifungal , algorithm , medicine , materials science , dermatology , computer science , economics , financial economics , metallurgy
We have devised an expeditious, efficient, asymmetric synthesis of the C(33) – C(37) fragment of amphotericin B that proceeds in 14 steps and 16% overall yield from tiglic aldehyde (( E )‐2‐methylbut‐2‐enal) with complete stereocontrol. The route described herein relies on the application of recently developed methods in catalytic asymmetric synthesis for stereocontrol through enantio‐ and diastereoselective functionalization of a substituted sorbate derivative.