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Enantiospecific Total Syntheses of (+)‐Hapalindole H and (−)‐12‐ epi ‐Hapalindole U
Author(s) -
Dethe Dattatraya H.,
Das Saikat,
Kumar Vijay B.,
Mir Nisar A.
Publication year - 2018
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201800970
Subject(s) - regioselectivity , chemistry , intramolecular force , allylic rearrangement , total synthesis , epoxide , lewis acids and bases , stereochemistry , nucleophilic addition , steric effects , organic chemistry , medicinal chemistry , catalysis
Enantiospecific total syntheses of (+)‐hapalindole H and (−)‐12‐ epi ‐hapalindole U as well as the formal syntheses of (+)‐hapalindole Q and (+)‐12‐ epi ‐fischerindole U isothiocyanate have been described. Key steps of our approach feature expedient, highly regio‐ and diastereoselective Lewis acid catalyzed Friedel–Crafts reaction of indole with cyclic allylic alcohols and intramolecular reductive Heck reaction. Efficiency of the synthetic route also relies on an alkynyl aluminate complex driven regioselective nucleophilic epoxide opening from a sterically hindered site.