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Asymmetric synthesis of moiramide B

Abstract:
The first asymmetric synthesis of Moiramide B 1 is achieved using lithium amide 4 and pyrrolidinone auxiliary 5; pyrrolidinone auxiliary 5 is used to create the novel (S)-2-methyl-N-benzyloxysuccinimide 15 which is subsequently acylated with the highly reactive tert-butoxycarbonyl-protected N-carboxanhydride of L-valine (Boc-Val-NCA) under strongly basic conditions, without racemization, while lithium amide 4 is used to synthesize homochiral D-β-phenylalanine tert-butyl ester 8.
Publication status:
Published

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Publisher copy:
10.1039/cc9960001797

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Institution:
University of Oxford
Department:
Oxford, MPLS, Chemistry, Organic Chemistry
More by this author
Institution:
University of Oxford
Department:
Oxford, MPLS, Chemistry, Organic Chemistry
Journal:
CHEMICAL COMMUNICATIONS
Issue:
15
Pages:
1797-1798
Publication date:
1996-08-07
DOI:
EISSN:
1364-548X
ISSN:
1359-7345
URN:
uuid:55a1d71e-eefc-42b2-b265-5f2b0f55e01f
Source identifiers:
45342
Local pid:
pubs:45342
Language:
English

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