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An Enantiodivergent Synthesis of Both Enantiomers of the Macrocyclic Lactone Curvularin

✍ Scribed by Bracher, Franz ;Schulte, Brigitte

Publisher
John Wiley and Sons
Year
1997
Tongue
English
Weight
378 KB
Volume
1997
Category
Article
ISSN
0947-3440

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✦ Synopsis

Abstract

The macrocyclic lactone (S)‐curvularin (10) and its enantiomer ent‐10 were prepared in an enantiodivergent manner from (S)‐methyl 7‐hydroxyoctanoate (4), which was easily obtained on two different ways. Esterification of 4 under either retention or inversion of the chiral centre gave the enantiomeric diesters 7 and ent‐7. Chemoselective cleavage of the methyl ester groups of these diesters followed by intramolecular acylation and O‐debenzylation gave the two enantiomers of curvularin.

πŸ“œ SIMILAR VOLUMES

ChemInform Abstract: An Enantiodivergent
ChemInform Abstract: An Enantiodivergent Synthesis of Both Enantiomers of the Macrocyclic Lactone Curvularin.
✍ F. BRACHER; B. SCHULTE πŸ“‚ Article πŸ“… 2010 πŸ› John Wiley and Sons βš– 32 KB πŸ‘ 2 views

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