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Enantioselective syntheses of (+)-methyl nonactate and (−)-methyl 8-epi-nonactate via asymmetric cycloadditive route

✍ Scribed by Byeang Hyean Kim; Ju Young Lee

Book ID
104225208
Publisher
Elsevier Science
Year
1992
Tongue
French
Weight
289 KB
Volume
33
Category
Article
ISSN
0040-4039

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✦ Synopsis

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 ionophoric macrotetrolide antibiotic isolated from a variety of Streptomyces cultures.' It is composed of two subunits of (+)-nonactic acid and two subunits of (-)-nonactic acid. amurged in an alternating order (S,symmetry).z

There have been many reported syntheses of nonactic acid derivatives in both optically active and racemic form with varying success with respect to the degree of stereoselectivity.

📜 SIMILAR VOLUMES

Stereoselective synthesis of (±)-methyl
Stereoselective synthesis of (±)-methyl nonactate and (±)-methyl 8-epi-nonactate.
✍ Barry Lygo; Norval O'Connor 📂 Article 📅 1987 🏛 Elsevier Science 🌐 French ⚖ 244 KB

+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.