Journal
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 136, Issue 19, Pages 6943-6951Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ja411942h
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Funding
- MICINN
- Regional Government of Andalucia [P09-FQM-4571]
- Spanish MICINN [CTQ-2011.22455]
- University of Granada (CEI-BIOTIC)
- Factoria de Cristalizacion, CONSOLIDER INGENIO
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We describe a new strategy to control the number of cyclization steps in bioinspired radical (poly)cyclizations involving epoxypolyenes containing keto units positioned along the polyene chain. This approach provides an unprecedentedly straightforward access to natural terpenoids with pendant unsaturated side chains. Additionally, in the case of bi- and tricyclizations, decalins with cis stereochemistry have been obtained as a consequence of the presence of the ketone. The preferential formation of cis-fused adducts was rationalized using DFT calculations. This result is completely unprecedented in biomimetic cyclizations and permits the access to natural terpenoids with this stereochemistry, as well as to non-natural analogues.
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