Concise Syntheses of Coronarin A, Coronarin E, Austrochaparol and Pacovatinin A
| Autor: | Mikio Fujii, Takahiro Miyake, Masako Kinoshita, Hiroyuki Akita, Keisuke Uda |
|---|---|
| Rok vydání: | 2008 |
| Předmět: |
chemistry.chemical_classification
Aldehydes Allylic rearrangement Magnetic Resonance Spectroscopy Spectrophotometry Infrared Nitrile Chemistry Stereochemistry Enantioselective synthesis Total synthesis Stereoisomerism General Chemistry General Medicine Nuclear magnetic resonance spectroscopy Naphthalenes Aldehyde Mass Spectrometry chemistry.chemical_compound Zingiberaceae Coronarin E Drug Discovery Indicators and Reagents Diterpenes Furans |
| Zdroj: | Chemical and Pharmaceutical Bulletin. 56:398-403 |
| ISSN: | 1347-5223 0009-2363 |
| DOI: | 10.1248/cpb.56.398 |
| Popis: | Total syntheses of (+)-coronarin A (1), (+)-coronarin E (2), (+)-austrochaparol (3) and (+)-pacovatinin A (4) were achieved from the synthetic (+)-albicanyl acetate (6). Dess-Martin oxidation of (+)-albicanol (5) derived from the chemoenzymatic product (6) gave an aldehyde (7), which was subjected to Julia one-pot olefination using beta-furylmethyl-heteroaromatic sulfones (8 or 9 ) gave (+)-trans coronarin E (2) and (+)-cis coronarin E (12) with high cis-selectivity. The synthesis of (+)-coronarin A (1) from (+)-trans coronarin E (2) was achiev-ed, while (+)-cis coronarin E (12) was converted to the natural products (+)-(5S,9S,10S)-15,16-epoxy-8(17),13(16),14-labdatriene (13) and (+)-austrochaparol (3). By the asymmetric synthesis of (+)-3, the absolute structure of (+)-3 was determined to be 5S, 7R, 9R, 10S configurations. Homologation of (+)-albicanol (5) followed by allylic oxidation gave (7 alpha)-hydroxy nitrile (17), which was finally converted to the natural (+)-pacovatinin A (4) in 8 steps from (+)-albicanol (5). |
| Databáze: | OpenAIRE |
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