Literature DB >> 23131084

Asymmetric total synthesis of an iboga-type indole alkaloid, voacangalactone, newly isolated from Voacanga africana.

Masaya Harada1, Ken Nunettsu Asaba, Masumi Iwai, Noriyuki Kogure, Mariko Kitajima, Hiromitsu Takayama.   

Abstract

A new hexacyclic iboga-type indole alkaloid, voacangalactone (1), was isolated from Voacanga africana , and its structure including the absolute configuration was established by asymmetric total synthesis involving such key steps as the asymmetric Diels-Alder reaction using an aminodiene and the construction of an isoquinuclidine ring and an indole skeleton.

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Year:  2012        PMID: 23131084     DOI: 10.1021/ol3027945

Source DB:  PubMed          Journal:  Org Lett        ISSN: 1523-7052            Impact factor:   6.005


  4 in total

Review 1.  The iboga enigma: the chemistry and neuropharmacology of iboga alkaloids and related analogs.

Authors:  Rishab N Iyer; David Favela; Guoliang Zhang; David E Olson
Journal:  Nat Prod Rep       Date:  2021-03-04       Impact factor: 13.423

2.  Efficient Access to the Iboga Skeleton: Optimized Procedure to Obtain Voacangine from Voacanga africana Root Bark.

Authors:  Bruno González; Catherine Fagúndez; Alejandro Peixoto de Abreu Lima; Leopoldo Suescun; Diver Sellanes; Gustavo A Seoane; Ignacio Carrera
Journal:  ACS Omega       Date:  2021-06-24

3.  Practical synthesis of indoles and benzofurans in water using a heterogeneous bimetallic catalyst.

Authors:  Cybille Rossy; Eric Fouquet; François-Xavier Felpin
Journal:  Beilstein J Org Chem       Date:  2013-07-16       Impact factor: 2.883

4.  Enantioselective synthesis of Iboga alkaloids and vinblastine via rearrangements of quaternary ammoniums.

Authors:  Yun Zhang; Yibin Xue; Gang Li; Haosen Yuan; Tuoping Luo
Journal:  Chem Sci       Date:  2016-05-16       Impact factor: 9.825

  4 in total

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