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Concise Catalytic Asymmetric Total Synthesis of Biologically Active Tropane Alkaloids
Author(s) -
Córdova Armando,
Lin Shuangzheng,
Tseggai Abrehet
Publication year - 2012
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201100917
Subject(s) - chemistry , tropane , enantioselective synthesis , total synthesis , catalysis , stereoselectivity , derivative (finance) , alkaloid , stereochemistry , combinatorial chemistry , organic chemistry , financial economics , economics
A general strategy for the total asymmetric synthesis of valuable tropane alkaloids by catalytic stereoselective transformations is disclosed. The power of this approach is exemplified by the concise catalytic enantioselective total syntheses of (+)‐methylecgonine, (−)‐cocaine and (+)‐cocaine as well as the first catalytic asymmetric total syntheses of a cocaine C‐1 derivative and (+)‐ferruginine starting from 5‐oxo‐protected‐α,β‐unsaturated enals using only two and three column chromatographic purification steps, respectively.