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

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...

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Published inJournal of organic chemistry Vol. 86; no. 9; pp. 6160 - 6168
Main Authors Gramani, Subramanian G, Sriramula, Ravi K, Sekar, Karthik, Yang, Eugene G, Battu, Praveena, Kopecky, Aïcha, Lear, Martin J
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 07.05.2021
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
CORE
RING-CLOSING METATHESIS
NATURAL-PRODUCTS
CONSTRUCTION
OLEFIN METATHESIS
EFFICIENT
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Summary: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.
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
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ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.0c02984