Synthesis and Absolute Configuration of (−)-Normalindine

✍ Scribed by Masashi Ohba; Hiroyuki Kubo; Tozo Fujii; Hiroyuki Ishibashi; Melvyn V. Sargent; Dayar Arbain

• Publisher: Elsevier Science
• Year: 1997
• Tongue: French
• Weight: 625 KB
• Volume: 38
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(97)01568-2

✦ Synopsis

Thefnt chiralsynthesisof the SoychnosandOpldorrhiza atkatoid(-)-normalindinehas been accomplishedthrougha routestartingfromL-atanine methylesterandexploitingintramolecular oxazobolefin Diels-Ahlerreaction.As a reauktheabsolutestereochemistry of nonnatindine hasken lk.finedasrqneaentedbyfords (-)-1. 01997 ElsevierScienceLtd.

(-)-Norm~in~ne (1), a member of the alk~oids containingthe indolo[2',3':3,41pyrido[ l,2-blmipMtyridine ring system,] was firat isolated by Massiot et al. in 1987from the root bark of Srrychnosjohnsonii (Loganiaceae).2The structureand relativestereochemical assignment,basedon its spectralproperties,were subsequentlyconfirmedby tworacemicsynthesesof 1.3 ThereafterArbainet al. also reported the isolationof thisalkaloidfromthe leavesof Ophiorrhizafilisfipula (Rubiaceae)andinferredits absolutecom@uration to be (-)-1 on the basis of CD spectralevidence.4 With a view to verifyingthe correctnessof this inference,we accomplisheda chiralsynthesisof thetargetcompound(-)-1 in thepresent work.