Journal
ORGANIC & BIOMOLECULAR CHEMISTRY
Volume 10, Issue 22, Pages 4462-4466Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/c2ob25453k
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Funding
- Board of Research in Nuclear Sciences (BRNS), Government of India [2009/37/25 BRNS]
- Department of Science and Technology New Delhi (DST) [SR/S1/OC-25/2008]
- Council of Scientific and Industrial Research (CSIR), New Delhi
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A stereoselective synthesis of (-)-1-epi-ventiloquinone L and (+)-ventiloquinone L, the monomeric unit of cardinalin 3 has been described. The synthesis is completed in 7 steps with 10.5% and 13% overall yields for (-)-1-epi-ventiloquinone L and (+)-ventiloquinone L respectively. The key steps involve Dotz benzannulation of carbene 5 with alkyne 6 to give a substituted naphthalene moiety and oxa-Pictet-Spengler reaction to install the 1,3-dimethylpyran moiety.
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