Total Synthesis of (−)-Sinulariadiolide. A Transannular Approach

Meng, Zhanchao; Fürstner, Alois

doi:10.1021/jacs.8b12185

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Total Synthesis of (−)-Sinulariadiolide. A Transannular Approach

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Meng, Zhanchao
Research Department Fürstner, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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Fürstner, Alois
Research Department Fürstner, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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引用

Meng, Z., & Fürstner, A. (2019). Total Synthesis of (−)-Sinulariadiolide. A Transannular Approach. Journal of the American Chemical Society, 141(2), 805-809. doi:10.1021/jacs.8b12185.

引用: https://hdl.handle.net/21.11116/0000-0002-DC96-D

要旨

The constrained tricyclic skeleton of the nor-cembranoid sinulariadiolide (1) with a nine-membered nexus was obtained by a cascade of transannular Michael reaction, carbonate elimination, butenolide formation, and spontaneous oxa-Michael addition of MeOH. The required macrocyclic precursor was prepared by ring-closing alkyne metathesis followed by trans-hydrostannation/carbonylation.