Synthesis of (+)-calanolide A, an anti-HIV agent, via enzyme-catalyzed resolution of the aldol products

…, S Dzekhtser, D Brankovic, H Zhang, W Chen…

Index: 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 Tetrahedron Asymmetry, 1996 , vol. 7, # 11 p. 3315 - 3326

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Citation Number: 39

Abstract

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 ...

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