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Toward an Asymmetric Synthesis of Bistramide K
Author(s) -
Bauder Claude
Publication year - 2018
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.201800875
Subject(s) - stereocenter , chemistry , sulfoxide , stereoselectivity , chirality (physics) , stereochemistry , metabolite , enantioselective synthesis , organic chemistry , biochemistry , catalysis , chiral symmetry breaking , physics , quantum mechanics , quark , nambu–jona lasinio model
The bistramides family has shown antitumoral activity. More specifically bistramide K exhibits lower toxicity than its congeners. In this work, we describe a highly stereoselective and convergent synthesis of two building blocks of the marine metabolite bistramide K. Thus, we report the synthesis of fragments C1–C18 ( 89 ) and C19–C40 ( 81 ) of bistramide K. As a challenge, we have used nonracemic methyl p ‐tolyl sulfoxide as unique source of chirality for the elaboration of all stereogenic centers of the natural compound.