Journal ArticleDOI
Synthesis, chromatographic resolution, and anti-human immunodeficiency virus activity of (±)-calanolide A and its enantiomers
Michael T. Flavin,John D. Rizzo,Albert Khilevich,Alla Kucherenko,Abram Kivovich Sheinkman,Vilayphone Vilaychack,Lin Lin,Wei Chen,Eugenia Mata Greenwood,Thitima Pengsuparp,John M. Pezzuto,Stephen H. Hughes,Thomas M. Flavin,Michael Cibulski,William A. Boulanger,Robert L. Shone,Ze-Qi Xu +16 more
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TLDR
The anti-HIV agent (+/-)-calanolide A (1) has been synthesized in a five-step approach starting with phloroglucinol, which includes Pechmann reaction, Friedel-Crafts acylation, chromenylation with 4,4-dimethoxy- 2-methylbutan-2-ol, cyclization, and Luche reduction.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 trifluoroacetic acid and pyridine or PPTS. Luche reduction of chromanone 18 at lower temperature preferably yielded (±)-1. Reduction of chromone 12, synthesized by Kostanecki−Robinson reaction from chromene 11, failed to afford (±)-1. The synthetic (±)-1 has been chromatographically resolved into its optically active forms, (+)- and (−)-1. The anti-HIV activities for synthetic (±)-1, as well as resultant (+)- and (−)-1, have been determined. Only (+)-1 accounted for anti-HIV activity, which was similar to the data reported for the natural product, and (−)-1 was inactive.read more
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Synthesis, experimental and theoretical studies on highly functionalized novel 4H-pyran-3-carboxylate
Chandran Udhaya Kumar,Muthiah Pillai Velayutham Pillai,Kannan Gokula Krishnan,Chennan Ramalingan +3 more
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