Literature DB >> 19634325

DMD mediated formal synthesis of (+/-)-coerulescine.

Oscar R Suárez-Castillo1, Myriam Meléndez-Rodríguez, Yaneth M A Contreras-Martínez, Alejandro Alvarez-Hernández, Martha S Morales-Ríos, Pedro Joseph-Nathan.   

Abstract

A highly efficient method for the formal synthesis of the natural product (+/-)-coerulescine 1 from tetrahydro-beta-carboline 3, mediated by dimethyldioxirane (DMD), is described. Compound 15, the N9-demethylated precursor of 1, was prepared from 3 in 4 steps with an overall yield of 95%. The effect of electron withdrawing groups at the N2,N9 atoms of 3 was explored for the oxidative rearrangement step.

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Year:  2009        PMID: 19634325

Source DB:  PubMed          Journal:  Nat Prod Commun        ISSN: 1555-9475            Impact factor:   0.986


  1 in total

1.  Total synthesis of (±)-coerulescine and (±)-horsfiline.

Authors:  Mukund G Kulkarni; Attrimuni P Dhondge; Sanjay W Chavhan; Ajit S Borhade; Yunnus B Shaikh; Deekshaputra R Birhade; Mayur P Desai; Nagorao R Dhatrak
Journal:  Beilstein J Org Chem       Date:  2010-09-27       Impact factor: 2.883

  1 in total

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