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10‐Step Asymmetric Total Synthesis and Stereochemical Elucidation of (+)‐Dragmacidin D
Author(s) -
Jackson Jeffrey J.,
Kobayashi Hiroyuki,
Steffens Sophia D.,
Zakarian Armen
Publication year - 2015
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201504113
Subject(s) - stereocenter , chemistry , alkylation , enantioselective synthesis , indole test , reagent , stereochemistry , total synthesis , trimethylsilyl , lithium (medication) , keto–enol tautomerism , tetramine , combinatorial chemistry , organic chemistry , catalysis , medicine , tautomer , endocrinology
The asymmetric synthesis of dragmacidin D ( 1 ) was completed in 10 steps. Its sole stereocenter was set by using direct asymmetric alkylation enabled by a C 2 ‐symmetric tetramine and lithium N ‐(trimethylsilyl)‐ tert ‐butylamide as the enolization reagent. A central Larock indole synthesis was employed in a convergent assembly of the heterocyclic subunits. The stereochemical evidence from this work strongly supports the predicted S configuration at the 6′′′ position, which is consistent with other members of the dragmacidin family of natural products.