A highly enantioselective synthesis of the indolizidine alkaloid 239AB is described via the diastereoselective reduction of a chiral cyclic 13-enamino ester prepared from (S)-pyroglutamic acid.
Enantioselective synthesis of indolizidine (−) 237A [(3R,5S,8aR)-3-butyl-5-(1-oxopropyl)-octahydroindolizine]
✍ Scribed by Giang Vo Thanh; Jean-Pierre Célérier; Gérard Lhommet
- Book ID
- 104261378
- Publisher
- Elsevier Science
- Year
- 1999
- Tongue
- French
- Weight
- 157 KB
- Volume
- 40
- Category
- Article
- ISSN
- 0040-4039
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✦ Synopsis
A highly enantioselective synthesis of the indolizidine alkaloid (-) 237A is described via the diastereoselective reduction of a heterocyclic enamine.
📜 SIMILAR VOLUMES
Enantioselective Synthesis of (-)-Indolizidine 239AB ((3R,5S,8aR)-3-Butyl-5-(3-hydroxypropyl)-octahydroindolizine). -A general synthesis for the title compound (XI) is presented as part of studies on the reactivity of chiral cyclic β-enamino esters, e. g. (II). (XI) belongs to a class of alkaloids
The title compound, C 12 H 22 N 2 O 6 , is a linearly fused di(trihydroxypiperido)piperazine. The three six-membered rings adopt chair conformations with all the hydroxyl groups equatorial, and the ring fusion is the unusual trans±cisoid±cis.