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A noncarbohydrate based approach to polyhydroxylated pyrrolidizines: total syntheses of the natural products hyacinthacine A1 and 1-epiaustraline.

Abstract:

[reaction: see text] A flexible route to polyhydroxylated pyrrolizidine alkaloids is described, starting from commercially available N-Boc pyrrole and using a partial reduction as the key step. Tactics for varying the stereochemistry around the ring by choice of partial reduction conditions are discussed and methods for constructing the bicyclic ring system of the pyrrolizidine targets are examined. Intramolecular S(N)2 type displacement reactions were found to be an efficient way of forming ...

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Publisher copy:
10.1021/jo050977s

Authors


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Institution:
University of Oxford
Department:
Oxford, MPLS, Chemistry, Organic Chemistry
Sintim, HO More by this author
Hollinshead, J More by this author
Journal:
J Org Chem
Volume:
70
Issue:
18
Pages:
7297-7304
Publication date:
2005-09-02
DOI:
EISSN:
1520-6904
ISSN:
0022-3263
URN:
uuid:78e4bc23-754e-4a90-b8bb-6b3bb97f3ab2
Source identifiers:
33210
Local pid:
pubs:33210

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