Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 79, Issue 21, Pages 10689-10695Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jo502048y
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Funding
- Spanish Ministry of Science and Innovation [CTQ 2009-09932]
- Regional Government of Andalucia [P07-FQM-03101, P11-CTS-7651]
- Spanish Ministry of Science and Innovation
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Synthesis of the putative structure of the marine natural 15-oxopuupehenoic acid has been achieved starting from commercial (-)-sclareol. Key steps of the synthetic sequence are the Robinson annulation of a beta-ketoester and methyl vinyl ketone and an unprecedented cyclization of the resulting a,beta-enone, which is mediated by tin(IV) chloride in the presence of N-phenylselenophthalimide. The physical properties of the synthetic compound are somewhat different from those reported for the natural product.
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