Premium
Enantioselective Synthesis of the C23–C33 Fragment of Aetheramide A and Its C32 Epimer
Author(s) -
Peňaška Tibor,
Koukal Petr,
Kotora Martin
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.201701416
Subject(s) - enantioselective synthesis , chemistry , epimer , stereochemistry , fragment (logic) , mandelic acid , organic chemistry , catalysis , computer science , programming language
The key aetheramide A intermediate with the natural ( R , R , R ) configuration along with the one having the unnatural ( R , S , R ) configuration was synthesized. The synthesis of both stereoisomers was accomplished by Suzuki coupling of two advanced chiral building blocks: ( R , R )‐ and ( R , S )‐vinylboronates and an ( R )‐iodoalkene. The former was prepared from ( R )‐mandelic acid, and the latter was prepared by enantioselective allylation of 3‐iodoacrylaldehyde.