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

Meng, Zhanchao; Fürstner, Alois

doi:10.1021/jacs.8b12185

Item

ITEM ACTIONSEXPORT

Add to Basket

Local TagsRelease HistoryDetailsSummary

Released

Journal Article

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

MPS-Authors

/persons/resource/persons223686

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

/persons/resource/persons58380

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

External Resource

No external resources are shared

Fulltext (restricted access)

There are currently no full texts shared for your IP range.

Fulltext (public)

There are no public fulltexts stored in PuRe

Supplementary Material (public)

ja8b12185_si_001-1_supporting information.pdf
(Supplementary material), 7MB

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: https://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.