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Issue 29, 2016
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Platinum-catalyzed cycloisomerizations of a common enyne: a divergent entry to cyclopropane sesquiterpenoids. Formal synthesis of sarcandralactone A

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Abstract

A common enyne scaffold, resembling the structures of natural elemanes was found to be an excellent substrate for highly regioselective cycloisomerizations to produce diverse cyclopropane sesquiterpenoids. Platinum-catalysis was utilized to produce either lindenane or myliol cores, found in natural products, starting from enyne acetate 10 and its corresponding allene 12 respectively. Based on this concept, a second generation strategy allows the formal synthesis of sarcandralactone A.

Graphical abstract: Platinum-catalyzed cycloisomerizations of a common enyne: a divergent entry to cyclopropane sesquiterpenoids. Formal synthesis of sarcandralactone A

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Article information


Submitted
06 Jun 2016
Accepted
22 Jun 2016
First published
22 Jun 2016

Org. Biomol. Chem., 2016,14, 6942-6946
Article type
Communication

Platinum-catalyzed cycloisomerizations of a common enyne: a divergent entry to cyclopropane sesquiterpenoids. Formal synthesis of sarcandralactone A

V. P. Demertzidou and A. L. Zografos, Org. Biomol. Chem., 2016, 14, 6942
DOI: 10.1039/C6OB01226D

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