Asymmetric Total Synthesis of (+)‐Bermudenynol, a C 15   Laurencia  Metabolite with a Vinyl Chloride Containing Oxocene Skeleton, through Intramolecular Amide Enolate Alkylation | Zendy

Kim Gyudong | Zendy; Sohn Teik | Zendy; Kim Deukjoon | Zendy; Paton Robert S. | Zendy

Premium

Asymmetric Total Synthesis of (+)‐Bermudenynol, a C 15 Laurencia Metabolite with a Vinyl Chloride Containing Oxocene Skeleton, through Intramolecular Amide Enolate Alkylation

Author(s) -

Kim Gyudong,

Sohn Teik,

Kim Deukjoon,

Paton Robert S.

Publication year - 2014

Publication title -

angewandte chemie international edition

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 5.831

H-Index - 550

eISSN - 1521-3773

pISSN - 1433-7851

DOI - 10.1002/anie.201308077

Subject(s) - intramolecular force , total synthesis , amide , chemistry , laurencia , alkylation , metabolite , ring closing metathesis , stereochemistry , metathesis , substrate (aquarium) , stereoselectivity , organic chemistry , biology , botany , polymerization , catalysis , ecology , biochemistry , polymer , algae

A substrate‐controlled asymmetric total synthesis of (+)‐bermudenynol, a compact and synthetically challenging C 15 Laurencia metabolite that contains several halogen atoms, is reported. The oxocene core, which contains a vinyl chloride, was constructed by an efficient and highly stereoselective intramolecular amide enolate alkylation (IAEA). This result showcases the broad utility of the IAEA methodology as a useful alternative for cases in which the ring‐closing metathesis is inefficient.

This content is not available in your region!

Continue researching here.

Having issues? You can contact us here

Accelerating Research