Enantioselective Total Synthesis of 1,3‐Disubstituted β‐Carboline Alkaloids, (–)‐Dichotomine A and (+)‐Dichotomide II | Zendy

Tagawa Shinji | Zendy; Choshi Tominari | Zendy; Okamoto Asuka | Zendy; Nishiyama Takashi | Zendy; Watanabe Shiroh | Zendy; Hatae Noriyuki | Zendy; Ishikura Minoru | Zendy; Hibino Satoshi | Zendy

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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 .

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