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

Subramanian G. Gramani | Zendy; Ravi K. Sriramula | Zendy; Karthik Sekar | Zendy; Eugene Guorong Yang | Zendy; Praveena Battu | Zendy; Aïcha Kopecky | Zendy; Martin J. Lear | Zendy

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

Author(s) -

Subramanian G. Gramani,

Ravi K. Sriramula,

Karthik Sekar,

Eugene Guorong Yang,

Praveena Battu,

Aïcha Kopecky,

Martin J. Lear

Publication year - 2021

Publication title -

the journal of organic chemistry

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 1.2

H-Index - 228

eISSN - 1520-6904

pISSN - 0022-3263

DOI - 10.1021/acs.joc.0c02984

Subject(s) - chemistry , steric effects , alkyne , ruthenium , ring closing metathesis , metathesis , stereochemistry , diol , catalysis , chelation , protein subunit , combinatorial chemistry , organic chemistry , biochemistry , gene , polymer , polymerization

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.

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