ChemInform Abstract: Total Synthesis of (-)-PA-48153C (Pironetin) Utilizing L-Quebrachitol as a Chiral Building Block.

✍ Scribed by N. CHIDA; M. YOSHINAGA; T. TOBE; S. OGAWA

• Publisher: John Wiley and Sons
• Year: 2010
• Weight: 37 KB
• Volume: 28
• Category: Article
• ISSN: 0931-7597
• DOI: 10.1002/chin.199741306

✦ Synopsis

Total Synthesis of (-)-PA-48153C (Pironetin) Utilizing L-Quebrachitol as a Chiral Building Block.

-An alternative approach to the novel immunosuppressant (XIV) is developed. The acyclic part (XI), containing four contiguous chiral centers, is constructed stereoselectively from L-quebrachitol (I). The 2-pyranone precursor (XII) is prepared from L-malic acid in five steps. Deprotection of the coupling product (XIII) followed by reduction of the ketone carbonyl affords the anti-diol as major product which is desilylated and oxidized to give the title compound. -(CHIDA, N.; YOSHINAGA, M.; TOBE, T.;