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

Accepted version
Peer-reviewed

Type

Article

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Authors

Gramani, Subramanian G  ORCID logo  https://orcid.org/0000-0002-8536-756X
Sriramula, Ravi K 
Sekar, Karthik 
Yang, Eugene G 
Battu, Praveena 

Abstract

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.

Description

Keywords

Catalysis, Diterpenes, Ruthenium

Journal Title

J Org Chem

Conference Name

Journal ISSN

0022-3263
1520-6904

Volume Title

Publisher

American Chemical Society (ACS)

Rights

All rights reserved