89923-31-9Relevant articles and documents
An efficient stereoselective total synthesis of 11β-methoxycurvularin
Yadav,Vani, C. Divya,Bhasker,Reddy, B.V. Subba
, p. 291 - 300 (2014/10/15)
A very short and efficient stereoselective total synthesis of a macrocyclic ketone, 11β-methoxycurvularin was achieved by employing the Sharpless asymmetric epoxidation, formation of propargyl alcohols from an epoxy-chloride, and intramolecular Friedel-Cr
Concise total synthesis of dihydrocorynanthenol, protoemetinol, protoemetine, 3-epi-protoemetinol and emetine
Lin, Shuangzheng,Deiana, Luca,Tseggai, Abrehet,Cordova, Armando
, p. 398 - 408 (2012/02/16)
A concise asymmetric assembly of secologanine tryptamine and dopamine alkaloids by means of a one-pot three-component cascade reaction methodology is disclosed. This is demonstrated by the expeditious total syntheses of (-)-dihydrocorynanthenol, (-)-protoemetinol, (-)-protoemetine, (-)-3-epi-protoemetinol, and emetine (3-6 steps). The biomimetic synthetic strategy involved the following key steps: (i) One-pot three-component highly enantioselective catalytic Michael/Pictet-Spengler/lactamization cascade reactions; (ii) One-pot tandem Swern oxidation/Wittig sequences; (iii) One-pot tandem hydrogenation sequences. Copyright
Diastereomerically and enantiomerically pure 2,3-disubstituted pyrrolidines from 2,3-aziridin-1-ols using a sulfoxonium ylide: A one-carbon homologative relay ring expansion
Schomaker, Jennifer M.,Bhattacharjee, Somnath,Yan, Jun,Borhan, Babak
, p. 1996 - 2003 (2007/10/03)
An ylide-based aza-Payne rearrangement of 2,3-aziridin-1-ols leads to an efficient process for the preparation of pyrrolidines. The aza-Payne rearrangement under basic reaction conditions favors the formation of epoxy amines. Subsequent nucleophilic attack of the epoxide by the ylide yields a bis-anion, which upon a 5-exo-tet ring-closure yields the desired pyrrolidine, thus completing the relay of the three-membered to the five-membered nitrogen-containing ring system. This process takes place with complete transfer of stereochemical fidelity and can be applied to sterically hindered aziridinols.
