Cis Selective RCM Study to the 14-Membered Cyclic Subunit of Bielschowskysin.

Autor: Gramani SG; Department of Chemistry, University of Cambridge, Lensfield Road, Cambridge CB2 1EW, U.K.; Department of Chemistry, National University of Singapore, 3 Science Drive 3, 117543, Singapore., Sriramula RK; Department of Chemistry, National University of Singapore, 3 Science Drive 3, 117543, Singapore., Sekar K; Department of Chemistry, National University of Singapore, 3 Science Drive 3, 117543, Singapore., Yang EG; Department of Chemistry, National University of Singapore, 3 Science Drive 3, 117543, Singapore., Battu P; Department of Chemistry, National University of Singapore, 3 Science Drive 3, 117543, Singapore., Kopecky A; Department of Chemistry, National University of Singapore, 3 Science Drive 3, 117543, Singapore., Lear MJ; Department of Chemistry, National University of Singapore, 3 Science Drive 3, 117543, Singapore.; School of Chemistry, University of Lincoln, Brayford Pool, Lincoln LN6 7TS, U.K.
Jazyk: angličtina
Zdroj: The Journal of organic chemistry [J Org Chem] 2021 May 07; Vol. 86 (9), pp. 6160-6168. Date of Electronic Publication: 2021 Apr 28.
DOI: 10.1021/acs.joc.0c02984
Abstrakt: A concise, ( Z )-selective ring-closing metathesis (RCM) route to the 14-membered carbocycle of bielschowskysin is detailed using naturally occurring chiral starting materials. Unproductive RCM substrates were attributed to alkyne chelation of the ruthenium catalyst and steric disadvantages within the cembranoid precursors, which was eventually circumvented by using cyclic diol benzylidene protection involving a C8-quaternary carbinol center.
Databáze: MEDLINE