263351-94-6Relevant articles and documents
Concise Synthesis of Anti-HIV-1 Active (+)-Inophyllum B and (+)-Calanolide A by Application of (-)-Quinine-Catalyzed Intramolecular Oxo-Michael Addition
Sekino, Etsuko,Kumamoto, Takuya,Tanaka, Tomohiro,Ikeda, Tomoko,Ishikawa, Tsutomu
, p. 2760 - 2767 (2007/10/03)
(-)-Quinine-catalyzed intramolecular oxo-Michael addition (IMA) of 7-hydroxy-5-methoxy-8-tigloylcoumarins was developed for the enantioselective construction of 2,3-dimethyl-4-chromanone systems in the context of the asymmetric synthesis of anti-HIV-1 act
PROCESSES FOR PREPARING CALANOLIDE A AND INTERMEDIATES THEREOF
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Page/Page column 20, (2008/06/13)
The present invention provides a production method of Calanolide A according to the following method wherein each symbol is as defined in the specification, as a more convenient and industrially practical method for the synthesis of Calanolide A from an easily available starting material.
Synthesis of (+)-calanolide A, an anti-HIV agent, via enzyme-catalyzed resolution of the aldol products
Khilevich, Albert,Mar, Aye,Flavin, Michael T.,Rizzo, John D.,Lin, Lin,Dzekhtser, Sergey,Brankovic, Darko,Zhang, Heping,Chen, Wei,Liao, Shuyuan,Zembower, David E.,Xu, Ze-Qi
, p. 3315 - 3326 (2007/10/03)
The synthesis of (+)-calanolide A (1), an anti-HIV-1 agent, is described. A TiCl4-mediated aldol reaction of compound 2 stereoselectively produced the desired syn diastereomer (±)-5, which was resolved by a lipase-catalyzed acylation reaction. Under Mitsunobu conditions (Ph3P/DEAD), the syn aldol product (+)-5 led to the formation of trans-2,3-dimethyl chroman-4-one [(+)-3] with 94% ee, while the anti aldol product (+)-6 yielded both trans and cis derivatives (+)-3 and (+)-4 with 60% and 68% ee, respectively. Luche reduction on (+)-3 led to (+)-1 and (+)-calanolide B in a ratio of 9:1. Copyright (C) Elsevier Science Ltd.