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Asymmetric synthesis of (-)-(1R,7aS)-absouline

Abstract:

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-amin...

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Publication status:
Published

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Publisher copy:
10.1016/j.tet.2012.11.080

Authors


More by this author
Institution:
University of Oxford
Division:
MPLS
Department:
Chemistry
Sub department:
Organic Chemistry
Role:
Author
More by this author
Institution:
University of Oxford
Division:
MPLS
Department:
Chemistry
Sub department:
Organic Chemistry
Role:
Author
Journal:
TETRAHEDRON More from this journal
Volume:
69
Issue:
4
Pages:
1369-1377
Publication date:
2013-01-28
DOI:
EISSN:
1464-5416
ISSN:
0040-4020
Language:
English
Keywords:
Pubs id:
pubs:368117
UUID:
uuid:09223a66-95d6-455a-95fe-31d64335ba0e
Local pid:
pubs:368117
Source identifiers:
368117
Deposit date:
2014-02-09

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