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Asymmetric syntheses of APTO and AETD: the β-amino acid fragments within microsclerodermins C, D, and E.

Abstract:
Efficient asymmetric syntheses of APTO and AETD, the highly functionalized β-amino acid fragments within microsclerodermins C, D, and E, are reported. The conjugate addition of lithium (R)-N-benzyl-N-(α-methylbenzyl)amide to tert-butyl (E,E)-7-(triisopropylsilyloxy)hepta-2,4-dienoate and in situ enolate oxidation with (-)-camphorsulfonyloxaziridine, diastereoselective dihydroxylation of a 2,3-syn-γ,δ-unsaturated-α-hydroxy-β-amino ester derivative under Donohoe conditions, and a Julia-Kocieński olefination were used as the key steps.
Publication status:
Published

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Publisher copy:
10.1021/jo302731m

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Institution:
University of Oxford
Division:
MPLS
Department:
Chemistry
Sub department:
Organic Chemistry
Role:
Author
Journal:
Journal of organic chemistry More from this journal
Volume:
78
Issue:
6
Pages:
2500-2510
Publication date:
2013-03-01
DOI:
EISSN:
1520-6904
ISSN:
0022-3263
Language:
English
Keywords:
Pubs id:
pubs:387103
UUID:
uuid:abbaeb3d-6832-45e3-b24e-1eabcae4ecfa
Local pid:
pubs:387103
Source identifiers:
387103
Deposit date:
2013-11-16

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