Lincoln Repository

Menu

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

Documents
Cis Selective RCM Study to the 14-Membered Cyclic Subunit of Bielschowskysin
Authors' Accepted Manuscript
  • Format: PDF
  • Size: 472kB
[img]
[Download]
[img]
Preview
 PDF
JOC 2021 - Lear.pdf - Whole Document
472kB
Item Type:Article
Item Status:Live Archive

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

Repository Staff Only: item control page