A General and Stereoselective Approach to Nonactate Esters and Isomers: A Versatile Synthesis of (+)-Methyl Nonactate. -The title compound (XIII), which is a subunit of the macrotetrolide antibiotic nonactin, is stereoselectively synthesized from the chiral hydroxyacetate (I) in 11 steps and 6.4% o
✦ LIBER ✦
A general and stereoselective approach to nonactate esters and isomers: A versatile synthesis of (+)-methyl nonactate
✍ Scribed by Gérard Mandville; Christian Girard; Robert Bloch
- Book ID
- 104208202
- Publisher
- Elsevier Science
- Year
- 1997
- Tongue
- French
- Weight
- 569 KB
- Volume
- 53
- Category
- Article
- ISSN
- 0040-4020
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✦ Synopsis
A total synthesis of (+)-methyl nonactate from a chiral synthon obtained by enantioselective enzymatic transesterification is described. This new approach involves stereoselective reactions of aldolisation, reduction and intramolecular Michael addition and appears to be quite general since it could be applied as well to the synthesis of both enantiomers of 2-or 8epi nonactate esters or homologues.
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