Cis Selective RCM Study to the 14-Membered Cyclic Subunit of Bielschowskysin.
Subramanian G GramaniRavi K SriramulaKarthik SekarEugene G YangPraveena BattuAïcha KopeckyMartin J LearPublished in: The Journal of organic chemistry (2021)
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.