Stereoselective synthesis of (±)-methyl nonactate and (±)-methyl 8-epi-nonactate.
✍ Scribed by Barry Lygo; Norval O'Connor
- Book ID
- 104227262
- Publisher
- Elsevier Science
- Year
- 1987
- Tongue
- French
- Weight
- 244 KB
- Volume
- 28
- Category
- Article
- ISSN
- 0040-4039
No coin nor oath required. For personal study only.
✦ Synopsis
+Metbyl nonactate (2) and (i)-methyl S-epi-nonactate (3), synthetic precursors to the antibiitic nonactin have been syntbcsised, employing the reaction of substituted epoxides with dianions derived from p-ketoesm as the key carbon-carbon bond-forming step.
📜 SIMILAR VOLUMES
Enantioselectiw routes to (+)-methyl nonactate (2) and (-)-m&y1 8-epi-nonactate (3) are described. The cornerstone of this synrktic strategy is a combination of asymmetric silyl tdtro~re cycloaddition and asymmetric reduction, which provides rhe key syn-1 &ii01 intermediate 4. ## Nonactin (1) is an
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