ChemInform Abstract: An Enantiodivergent Synthesis of Both Enantiomers of the Macrocyclic Lactone Curvularin.

✍ Scribed by F. BRACHER; B. SCHULTE

• Publisher: John Wiley and Sons
• Year: 2010
• Weight: 32 KB
• Volume: 28
• Category: Article
• ISSN: 0931-7597
• DOI: 10.1002/chin.199750252

✦ Synopsis

An Enantiodivergent Synthesis of Both Enantiomers of the Macrocyclic Lactone Curvularin.

-An enantiodivergent synthesis of curvularin (S)-(IX) and its enantiomer is presented based on the esterification of key intermediate (S)-(V) under either retention or inversion of the chiral center leading to (S)-and (R)-diesters (VII), respectively. The selective cleavage of the methyl ester group with 3 equiv. of NaCN, followed by intramolecular acylation and O-debenzylation, gives both title enantiomers. The hydroxy ester (IV) is obtained by two different procedures with similar yields. -(BRACHER, F.;