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; Lear, Martin J

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

Afiliação

Gramani SG; Department of Chemistry, University of Cambridge, Lensfield Road, Cambridge CB2 1EW, U.K.
Sriramula RK; Department of Chemistry, National University of Singapore, 3 Science Drive 3, 117543, Singapore.
Sekar K; Department of Chemistry, National University of Singapore, 3 Science Drive 3, 117543, Singapore.
Yang EG; Department of Chemistry, National University of Singapore, 3 Science Drive 3, 117543, Singapore.
Battu P; Department of Chemistry, National University of Singapore, 3 Science Drive 3, 117543, Singapore.
Kopecky A; Department of Chemistry, National University of Singapore, 3 Science Drive 3, 117543, Singapore.
Lear MJ; Department of Chemistry, National University of Singapore, 3 Science Drive 3, 117543, Singapore.

J Org Chem ; 86(9): 6160-6168, 2021 05 07.

Article em En | MEDLINE | ID: mdl-33908786

ABSTRACT

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.

Assuntos

Diterpenos; Rutênio; Catálise

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Texto completo: 1 Coleções: 01-internacional Base de dados: MEDLINE Assunto principal: Rutênio / Diterpenos Idioma: En Revista: J Org Chem Ano de publicação: 2021 Tipo de documento: Article País de afiliação: Reino Unido

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