Synthesis, chromatographic resolution, and anti-human immunodeficiency virus activity of (±)-calanolide A and its enantiomers

…, W Chen, EM Greenwood, T Pengsuparp…

Index: Flavin, Michael T.; Rizzo, John D.; Khilevich, Albert; Kucherenko, Alla; Sheinkman, Abram K.; Vilaychack, Vilayphone; Lin, Lin; Chen, Wei; Greenwood, Eugenia Mata; Pengsuparp, Thitima; Pezzuto, John M.; Hughes, Stephen H.; Flavin, Thomas M.; Cibulski, Michael; Boulanger, William A.; Shone, Robert L.; Xu, Ze-Qi Journal of Medicinal Chemistry, 1996 , vol. 39, # 6 p. 1303 - 1313

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Citation Number: 145

Abstract

The anti-HIV agent (±)-calanolide A (1) has been synthesized in a five-step approach starting with phloroglucinol [→ 5→ 6→ 11→ 18→(±)-1], which includes Pechmann reaction, Friedel-Crafts acylation, chromenylation with 4, 4-dimethoxy-2-methylbutan-2-ol, cyclization, and Luche reduction. Cyclization of chromene 11 to chromanone 18 was achieved by employing either acetaldehyde diethyl acetal or paraldehyde in the presence of ...