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The most efficient and concise asymmetric synthesis of (-)-(1R,7aS)- absouline to date, which was accomplished in eight steps and 20% overall yield from commercially available starting materials, is described. The doubly diastereoselective conjugate addition of lithium (S)-N-benzyl-N-(α- methylbenzyl)-amide to an enantiopure α,β-unsaturated ester derived from l-proline was employed as the key step. Subsequent hydrogenolytic N-debenzylation and acid-promoted cyclisation of the resultant β-amino ester produced the 1-aminopyrrolizidin-3-one scaffold, then reduction with DIBAL-H was followed by DCC-mediated coupling with (E)-p-methoxycinnamic acid to complete the synthesis of (-)-(1R,7aS)-absouline. © 2012 Elsevier Ltd. All rights reserved.

Original publication

DOI

10.1016/j.tet.2012.11.080

Type

Journal article

Journal

Tetrahedron

Publication Date

28/01/2013

Volume

69

Pages

1369 - 1377