Ethyl (1R*,10S*,12R*,15S*)-4-Hydroxy-2-oxo-15- (2-oxo-1-pyrrolidinyl)-9-oxatetracyclo[10.2.2.01,10.03,8]hexadeca-3,5,7,13-tetraene-13-carboxylate

HEREDIA MOYA, JORGE HUMBERTO; Ramiro Araya-Maturana

doi:10.3390/M928

Ethyl (1R,10S,12R,15S)-4-Hydroxy-2-oxo-15- (2-oxo-1-pyrrolidinyl)-9-oxatetracyclo[10.2.2.01,10.03,8]hexadeca-3,5,7,13-tetraene-13-carboxylate

Journal

Molbank

ISSN

1422-8599

Date Issued

2017-01-18

Author(s)

HEREDIA MOYA, JORGE HUMBERTO

Facultad de Ciencias de la Salud Eugenio Espejo

Ramiro Araya-Maturana

DOI

10.3390/M928

URL

https://cris.ute.edu.ec/handle/123456789/1037

Abstract

N-Vinylpirrolidinone reacts with (E)-ethyl 5-hydroxy-3-(4-oxo-4H-chromen-3-yl) acrylate (1) through a domino reaction similar to that reported reaction for ethyl vinyl ether. Inverse electron demand Diels–Alder (IEDDA)–elimination-IEDDA generates isomeric tetracycles 5 and 6. The assignment of the relative stereochemistry of the products was made by comparing the proton couplings with those obtained by reaction with ethyl vinyl ether.