Total synthesis of (-)-rosmarinecine by intramolecular cycloaddition of (S)-malic acid derived pyrroline N-oxide.
[reaction in text] Straightforward total syntheses of (-)-rosmarinecine have been achieved from L-malic acid derived pyrroline N-oxides by two novel useful cascade processes, which join the family of domino reactions. Both strategies, which furnished the target alkaloid in enantioenriched and enantiopure forms, respectively, allow complete control of configuration at all the three newly created contiguous stereogenic centers.
Goti
A
A
Dipartimento di Chimica organica "Ugo Schiff", Centro di Studio C.N.R. sulla Chimica e la Struttura dei Composti Eterociclici e loro Applicazioni (CSCEA), Università degli Studi di Firenze, via G. Capponi 9, I-50121 Firenze, Italy. goti@chimorg.unifi.it
Cacciarini
M
M
Cardona
F
F
Cordero
F M
FM
Brandi
A
A
D000470:Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D008293:Malates / Q000737:chemistry; D015394:Molecular Structure; D011758:Pyrroles / Q000737:chemistry; D011763:Pyrrolizidine Alkaloids; D013237:Stereoisomerism; D013329:Structure-Activity Relationship
D000470:Alkaloids; D008293:Malates; D011758:Pyrroles; D011763:Pyrrolizidine Alkaloids; C429134:hastanecine; C429133:rosmarinecine; C030298:malic acid