Vinyl imidates in cycloaddition reactions: a formal synthesis of (+/-)-reserpine.
[reaction: see text] The intramolecular Diels-Alder reaction of N-acylvinylimidates provides an efficient entry into cis-fused perhydroisoquinoline ring systems. This is demonstrated by the preparation of isoquinoline 2, an intermediate, which has been previously transformed to reserpine.
Sparks
S M
SM
Department of Chemistry, 516 Rowland Hall, University of California, Irvine, California 92697-2025, USA. kjshea@uci.edu
Shea
K J
KJ
D007096:Imidoesters / Q000737:chemistry*; D007546:Isoquinolines / Q000138:chemical synthesis*; D012110:Reserpine / Q000138:chemical synthesis*; D014753:Vinyl Compounds / Q000737:chemistry*
D007096:Imidoesters; D007546:Isoquinolines; D014753:Vinyl Compounds; D012110:Reserpine