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Asymmetric synthesis of (-)-(S,S)-homaline

Abstract:

The asymmetric synthesis of (-)-(S,S)-homaline was achieved in 8 steps from commercially available starting materials using the diastereoselective conjugate addition of the novel lithium amide reagent lithium (R)-N-(3-chloropropyl)-N-(α-methyl-p-methoxybenzyl)amide to methyl cinnamate to install the correct stereochemistry. Subsequent functional group manipulation of the resultant β-amino ester and Sb(OEt) 3- mediated macrolactamisation was followed by homodimerisatio...

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Publication status:
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Institution:
University of Oxford
Department:
Oxford, MPLS, Chemistry, Organic Chemistry
Role:
Author
More by this author
Institution:
University of Oxford
Department:
Oxford, MPLS, Chemistry, Organic Chemistry
Role:
Author
Journal:
TETRAHEDRON LETTERS
Volume:
53
Issue:
9
Pages:
1119-1121
Publication date:
2012-02-29
DOI:
EISSN:
1873-3581
ISSN:
0040-4039
URN:
uuid:06f618d1-a1c1-41c8-838d-a8fb2aa703b8
Source identifiers:
341453
Local pid:
pubs:341453

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