Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 53, Issue 32, Pages 8513-8517Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201403605
Keywords
ring-closing olefin metathesis; sesterterpenoids; stereoselective; synthesis; total synthesis
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Funding
- Fonds der Chemischen Industrie
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Nitidasin is a pentacyclic sesterterpenoid with a rare 5-8-6-5 carbon skeleton that was isolated from the Peruvian folk medicine Hercampuri. It belongs to a small class of sesterterpenoids that feature an isopropyl trans-hydrindane moiety fused to a variety of other ring systems. As a first installment of our general approach toward these natural products, we report the total synthesis of the title compound. Our stereoselective, convergent route involves the addition of a complex alkenyl lithium compound to a trans-hydrindanone, followed by chemoselective epoxidation, ring-closing olefin metathesis, and redox
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