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Journal Article

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

MPS-Authors
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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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ja8b12185_si_001-1_supporting information.pdf
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Citation

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.


Cite as: http://hdl.handle.net/21.11116/0000-0002-DC96-D
Abstract
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.