Premium
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 .