Total synthesis of (+/-)fasicularin via a 2-amidoacrolein cycloaddition.
The total synthesis of the cytotoxin fasicularin is described. The key steps include the following: (1) an intermolecular Diels-Alder cycloaddition of a 2-(triflamido)acrolein with the dioxolane ketal of trideca-1,3-dien-7-one to establish the trans-perhydroisoquinoline stereochemistry, (2) a stereoelectronically controlled hydride addition to a N(1)-C(2) iminium ion to introduce the equatorial hexyl substituent, and (3) elaboration of the pyrido ring by an internal aldol reaction.
Maeng
Jun-Ho
JH
Department of Chemistry, Pennsylvania State University, University Park, PA 16802, USA.
Funk
Raymond L
RL
D000171:Acrolein / Q000031:analogs & derivatives* / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D013861:Thiocyanates / Q000138:chemical synthesis* / Q000737:chemistry
D013861:Thiocyanates; C448329:fasicularin; D000171:Acrolein