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

Gramani, Subramanian G., Sriramula, Ravi K., Sekar, Karthik , Yang, Eugene G., Battu, Praveena, Kopecky, Aïcha and Lear, Martin (2021) Cis Selective RCM Study to the 14-Membered Cyclic Subunit of Bielschowskysin. Journal of Organic Chemistry, 86 (9). pp. 6160-6168. ISSN 0022-3263

Full content URL: https://doi.org/10.1021/acs.joc.0c02984

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

A concise, (Z)-selective ring-closing metathesis (RCM) route to the 14-membered carbocycle of bielschowskysin is detailed, using nat-urally occurring chiral starting materials. Unproductive RCM substrates were attributed to alkyne chelation of the ruthenium cata-lyst and steric disadvantages within the cembranoid precursors, which was eventually circumvented by using cyclic diol benzylidene protection involving a C8-quaternary carbinol centre.

Keywords:Total synthesis studies, organic chemistry
Subjects:F Physical Sciences > F160 Organic Chemistry
Divisions:College of Science > School of Chemistry
ID Code:44693
Deposited On:28 Apr 2021 16:01

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