Premium
Total Syntheses of rac ‐ and (+)‐Goniomitine
Author(s) -
Park Eunjoon,
Cheon CheolHong
Publication year - 2019
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201900801
Subject(s) - chemistry , aldimine , aldehyde , indole test , total synthesis , natural product , vinyl acetate , strecker amino acid synthesis , organic chemistry , stereochemistry , catalysis , enantioselective synthesis , copolymer , polymer
Concise total syntheses of rac ‐ and (+)‐goniomitine were developed. The cyanide‐catalyzed imino‐Stetter reaction of an aldimine, derived from ethyl 2‐aminocinnamate and either rac ‐ or ( S )‐ α , β ‐unsaturated aldehyde bearing a δ ‐valerolactam at the β ‐position, provided rac ‐ or ( S )‐indole‐3‐acetate carrying an α ‐vinyl‐ δ ‐valerolactam scaffold at the 2‐position, respectively. Subsequent saturation of the vinyl group, followed by treatment with DIBAL‐H, afforded N‐benzyl protected goniomitine. Final debenzylation provided the desired natural product after only three column separations.