Asymmetric Synthesis of the C1–C13 Fragment of the Marine Metabolite Bistramide K | Zendy

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Asymmetric Synthesis of the C1–C13 Fragment of the Marine Metabolite Bistramide K

Author(s) -

Bauder Claude

Publication year - 2010

Publication title -

european journal of organic chemistry

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.825

H-Index - 155

eISSN - 1099-0690

pISSN - 1434-193X

DOI - 10.1002/ejoc.201000881

Subject(s) - stereocenter , chemistry , olefin fiber , fragment (logic) , stereochemistry , aldehyde , pyran , metabolite , aldol reaction , enantioselective synthesis , organic chemistry , biochemistry , catalysis , algorithm , computer science

A synthetic study on the construction of the C1–C13 fragment of bistramide K is described. This unit differs from other members of the bistramide family, which are equipped with a pyran structure at C6–C11. In bistramide K, the linear C1–C13 portion contains three stereogenic centers as well as two supplementary ( E )‐olefin positions. The key step in the synthesis was the elaboration of the ( E )‐olefin C6–C7 by using a Julia–Kocienski reaction between aldehyde 4 and benzothiazolesulfone 15 .

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