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Asymmetric synthesis of (-)-martinellic acid.

Abstract:
A high-yielding total asymmetric synthesis of (-)-martinellic acid is reported. The conjugate addition of lithium (R)-N-allyl-N-(α-methyl-4-methoxybenzyl)amide to tert-butyl (E)-3-[2'-(N,N-diallylamino)-5'-bromophenyl]propenoate and alkylation of the resultant β-amino ester have been used as the key steps to install the C(9b) and C(3a) stereogenic centers, respectively, and a highly diastereoselective Wittig reaction/intramolecular Michael addition was then used to create the C(4) stereogenic center within this tricyclic molecular architecture.
Publication status:
Published

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Publisher copy:
10.1021/ol4007508

Authors


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Institution:
University of Oxford
Department:
Oxford, MPLS, Chemistry, Organic Chemistry
Fletcher, AM More by this author
Lorkin, TJ More by this author
More by this author
Institution:
University of Oxford
Department:
Oxford, MPLS, Chemistry, Organic Chemistry
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Journal:
Organic letters
Volume:
15
Issue:
8
Pages:
2050-2053
Publication date:
2013-04-05
DOI:
EISSN:
1523-7052
ISSN:
1523-7060
URN:
uuid:05a2fb1d-aa19-47dd-b450-5373080e77cd
Source identifiers:
394909
Local pid:
pubs:394909

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