- 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
- Publisher copy:
- 10.1021/ol4007508
-
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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
- Language:
- English
- Keywords:
- Copyright date:
- 2013
Journal article
Asymmetric synthesis of (-)-martinellic acid.
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