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Synlett 2012; 23(20): 2951-2956
DOI: 10.1055/s-0032-1317622
letter
© Georg Thieme Verlag Stuttgart · New York

Synthesis of Nuevamine Aza-Analogues by a Sequence: I-MCR–Aza-Diels–Alder–Pictet–Spengler

Alejandro Islas-Jácome
a   Departamento de Química, División de Ciencias Básicas e Ingeniería, Universidad Autónoma Metropolitana-Iztapalapa, San Rafael Atlixco 186, Col. Vicentina Iztapalapa, C. P. 09340, México D. F., México   Fax: +52(55)58044666   eMail: egz@xanum.uam.mx
b   Departamento de Química, División de Ciencias Naturales y Exactas, Universidad de Guanajuato, Noria Alta S/N, Col. Noria Alta, C. P. 36050, Guanajuato, Guanajuato, México   Fax: +52(473)73200068168   eMail: rociogm@ugto.mx
,
Luis E. Cárdenas-Galindo
b   Departamento de Química, División de Ciencias Naturales y Exactas, Universidad de Guanajuato, Noria Alta S/N, Col. Noria Alta, C. P. 36050, Guanajuato, Guanajuato, México   Fax: +52(473)73200068168   eMail: rociogm@ugto.mx
,
Alberto V. Jerezano
c   Departamento de Química Orgánica, Escuela Nacional de Ciencias Biológicas, Instituto Politécnico Nacional, Prol. Carpio y Plan de Ayala S/N, Col. Casco de Santo Tomás, C. P. 11340, México D. F., México
,
Joaquín Tamariz
c   Departamento de Química Orgánica, Escuela Nacional de Ciencias Biológicas, Instituto Politécnico Nacional, Prol. Carpio y Plan de Ayala S/N, Col. Casco de Santo Tomás, C. P. 11340, México D. F., México
,
Eduardo González-Zamora*
a   Departamento de Química, División de Ciencias Básicas e Ingeniería, Universidad Autónoma Metropolitana-Iztapalapa, San Rafael Atlixco 186, Col. Vicentina Iztapalapa, C. P. 09340, México D. F., México   Fax: +52(55)58044666   eMail: egz@xanum.uam.mx
,
Rocío Gámez-Montaño*
b   Departamento de Química, División de Ciencias Naturales y Exactas, Universidad de Guanajuato, Noria Alta S/N, Col. Noria Alta, C. P. 36050, Guanajuato, Guanajuato, México   Fax: +52(473)73200068168   eMail: rociogm@ugto.mx
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Publikationsverlauf

Received: 03. September 2012

Accepted after revision: 24. Oktober 2012

Publikationsdatum:
23. November 2012 (online)

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Abstract

A series of nuevamine aza-analogues were prepared in moderate to good yields in two reaction steps. The synthetic strategy involves an isonitrile-based multicomponent reaction, including an aza-Diels–Alder cycloaddition and Pictet–Spengler reaction as postcondensation.

Key words

nuevamine aza-analogue - I-MCR - aza-Diels–Alder - S-oxidation - Pictet–Spengler cyclization
 

  • References and Notes

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