A Highly Convergent Total Synthesis of (+)-Compactin

Article abstract of DOI:10.1021/jo00363a016

An intramolecular Diels-Alder approach to the construction of (+)-compactin is described.Alkylation of the lithium enolate of (acetylmethylene)triphenylphosphorane with the tosylate of allenic alcohol 15 affords phosphorane 16, which condenses with aldehyde 6 (prepared from tri-O-acetyl-D-glucal) to afford enone 3.Intramolecular Diels-Alder reaction, reduction with lithium tri-sec-butylborohydride, and acylation with (S)-(+)-2-methylbutyric anhydride yields a chromatographically separable mixture of diastereomers; conversion to compactin was accomplished by acid hydrolysis followed by oxidation.