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Inside Cover: Stereoselective Synthesis of the Halaven C14–C26 Fragment from D ‐Quinic Acid: Crystallization‐Induced Diastereoselective Transformation of an α‐Methyl Nitrile (Angew. Chem. Int. Ed. 17/2015)
Author(s) -
Belanger Francis,
Chase Charles E.,
Endo Atsushi,
Fang Francis G.,
Li Jing,
Mathieu Steven R.,
Wilcoxen Annie Z.,
Zhang Huiming
Publication year - 2015
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Reports
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201502751
Subject(s) - fragment (logic) , stereoselectivity , chemistry , stereochemistry , combinatorial chemistry , quinic acid , crystallization , limiting , total synthesis , computer science , organic chemistry , catalysis , engineering , programming language , mechanical engineering
Crystallization by design enables the industrial synthesis of the hitherto expensive and throughput‐limiting fragment (C14–C26) for the construction of the structurally complex marine natural product inspired breast‐cancer drug Halaven. In their Communication on page 5108 ff., F. G. Fang et al. describe a number of stereoselective transformations on a crystalline polycyclic template derived from D ‐quinic acid (picture of Halichondria okadai : Prof. Uemura, Kanagawa University).