4017-77-0Relevant articles and documents
Enantiospecific Total Syntheses of (+)-Hapalindole H and (?)-12-epi-Hapalindole U
Dethe, Dattatraya H.,Das, Saikat,Kumar, Vijay B.,Mir, Nisar A.
, p. 8980 - 8984 (2018/06/04)
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.
Enantiospecific total syntheses and assignment of absolute configuration of cannabinol-skeletal carbazole alkaloids murrayamines-O and -P
Dethe, Dattatraya H.,Das, Saikat,Dherange, Balu D.,Mahapatra, Samarpita
, p. 8347 - 8350 (2015/06/02)
First enantiospecific total syntheses of the cannabinol-skeletal carbazole alkaloids murrayamines-O and -P isolated from root barks of Murraya euchrestifoli, have been accomplished by highly diastereoselective, Lewis acid catalyzed coupling reactions of commercially available monoterpenes with carbazole derivative, which in addition to confirming the structure also established the absolute configuration of the natural products. Synthesis of both natural products and their enantiomers was achieved with high atom economy, in a protecting-group free manner and in six steps longest linear sequence from commercially available aniline derivative and verbenol.
Lipase-catalyzed resolution of p-menthan-3-ols monoterpenes: Preparation of the enantiomer-enriched forms of menthol, isopulegol, trans- and cis-piperitol, and cis-isopiperitenol
Serra, Stefano,Brenna, Elisabetta,Fuganti, Claudio,Maggioni, Francesco
, p. 3313 - 3319 (2007/10/03)
A study on the enzymic resolution of the most common p-menthan-3-ol monoterpene isomers is described. Enantioenriched alcohols 1, 5, 10, 11 and 12 are obtained by means of the lipase-mediated kinetic acetylation of the corresponding racemic materials. The stereochemical aspects of the enzymic process have been investigated. We found that the structural features of the starting p-menthan-3-ol as well as the kind of lipase used, impacted strongly on the enantioselectivity of the resolution. The potentialities of this approach for preparative purposes are discussed.
