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Total Syntheses of Dichotomines A–D and the Stereochemical Revision of Dichotomines B–D
Author(s) -
Zhang Qiang,
Dong Jing,
Shi XiaoXin,
Lu Xia
Publication year - 2012
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.201200235
Subject(s) - stereocenter , chemistry , absolute configuration , stereochemistry , conjugate , glyceraldehyde , total synthesis , enantioselective synthesis , organic chemistry , catalysis , mathematical analysis , mathematics , dehydrogenase , enzyme
New asymmetric total syntheses of (–)‐dichotomines A–D ( 1 – 4 ) starting from L ‐tryptophan methyl ester and 2,3‐ O ‐isopropylidene‐ D ‐glyceraldehyde are described. The absolute configuration of the stereogenic center of (–)‐dichotomine A ( 1 ) was reconfirmed as ( S ), on the basis of the X‐ray crystallographic analysis of the conjugate (i.e., 17 ) of its methyl ester (i.e., 16 ) with ( S )‐ N ‐tosylproline, whereas the absolute configurations of the stereogenic centers of (–)‐dichotomines B–D ( 2 – 4 ) were revised as ( R ).
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