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Enantioselective Total Synthesis of 1,3‐Disubstituted β‐Carboline Alkaloids, (–)‐Dichotomine A and (+)‐Dichotomide II
Author(s) -
Tagawa Shinji,
Choshi Tominari,
Okamoto Asuka,
Nishiyama Takashi,
Watanabe Shiroh,
Hatae Noriyuki,
Ishikura Minoru,
Hibino Satoshi
Publication year - 2013
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201201652
Subject(s) - enantioselective synthesis , chemistry , stereocenter , enantiomer , stereochemistry , total synthesis , absolute configuration , lipase , organic chemistry , enzyme , catalysis
( S )‐(–)‐Dichotomine A and its enantiomer were synthesized from the key intermediate, methyl 1‐(1‐hydroxyethyl)‐β‐carboline‐3‐carboxylate, by enantioselective esterification with Lipase QLM. The first total synthesis of (+)‐dichotomide II and its enantiomer were also achieved from ( S )‐(–)‐dichotomine A methyl ester and its enantiomer. The absolute configuration of the stereogenic center of the reported (+)‐dichotomide II was determined to be R .