Category Archives: TosMIC

2026, Publicación, TosMIC

García-García et al. Org Lett. 2026;28(3):907-911. Synthesis of Multisubstituted Pyridines by Heterocyclization of TosMIC Derivatives: Total Synthesis of Caerulomycins A and K.

Publications > García-García et al

Org Lett. 2026 Jan 23;28(3):907-911. doi: 10.1021/acs.orglett.5c04454. Epub 2025 Dec 3. PubMed 41338582

Synthesis of Multisubstituted Pyridines by Heterocyclization of TosMIC Derivatives: Total Synthesis of Caerulomycins A and K.

José A García-García, José Luis Aceña, Patricia García-García, David Sucunza

Departamento de Química Orgánica y Química Inorgánica, Instituto de Investigación Química "Andrés M. del Río" (IQAR), Universidad de Alcalá, IRYCIS, 28805 Alcalá de Henares, Madrid, Spain.

Abstract

A concise synthesis of multisubstituted pyridines from α-allylic TosMIC derivatives and electrophiles is reported. The process involves a tandem heterocyclization exploiting the dual reactivity of the isocyanide group. The methodology tolerates various electrophiles, including halogen sources, and proceeds under mild conditions. Its utility is showcased in the total synthesis of caerulomycins A and K, in only five steps from TosMIC.

2023, Publicación, TosMIC

Maqueda-Zelaya et al. The Journal of Organic Chemistry. 2023;88(19):14131 -14139. 1,2,3-Benzotriazine Synthesis by Heterocyclization of p-Tosylmethyl Isocyanide Derivatives.

Publications > Maqueda-Zelaya et al

J. Org. Chem. 2023, 88, 14131

1,2,3-Benzotriazine Synthesis by Heterocyclization of p-Tosylmethyl Isocyanide Derivatives.

Francisco Maqueda-Zelaya, José Luis Aceña, Estíbaliz Merino, Juan J. Vaquero, David Sucunza

Resumen

No hay resumen

2018, Publicación, TosMIC

Gutierrez et al. J Org Chem. 2018;83(12):6623-6632. gamma-Carboline Synthesis by Heterocyclization of TosMIC Derivatives.

Publications > Gutierrez et al

J Org Chem. 2018, 83, 6623 PubMed 29756452

gamma-Carboline Synthesis by Heterocyclization of TosMIC Derivatives.

Sara Gutierrez, David Sucunza, Juan J Vaquero

Departamento de Quimica Organica y Quimica Inorganica and Instituto de Investigacion Quimica "Andres M. del Rio" (IQAR) , Universidad de Alcala , 28805 - Alcala de Henares , Madrid , Spain.

Abstract

A new method for the synthesis of gamma-carbolines by a heterocyclization that involves alpha-indol-2-ylmethyl TosMIC derivatives and different electrophiles has been developed. This methodology has been successfully applied to the synthesis of several highly substituted gamma-carbolines.

2016, Publicación, TosMIC

Gutierrez et al. Org Lett. 2016;18(14):3378-81. Synthesis of 1-Substituted Isoquinolines by Heterocyclization of TosMIC Derivatives: Total Synthesis of Cassiarin A.

Publications > Gutierrez et al

Org Lett. 2016, 18, 3378 PubMed 27351205

Synthesis of 1-Substituted Isoquinolines by Heterocyclization of TosMIC Derivatives: Total Synthesis of Cassiarin A.

Sara Gutierrez, Anna Coppola, David Sucunza, Carolina Burgos, Juan J Vaquero

Departamento de Quimica Organica y Quimica Inorganica, Universidad de Alcala , Alcala de Henares 28871, Spain.

Abstract

A new method for the synthesis of 1-substituted isoquinolines by a heterocyclization that involves alpha-benzyl TosMIC derivatives and different electrophiles has been developed. This methodology has been successfully applied to a total synthesis of cassiarin A, an alkaloid with potent antiplasmodial activity against Plasmodium falciparum.

2015, Publicación, TosMIC

Coppola et al. Org Lett. 2015;17(1):78-81. Isoquinoline synthesis by heterocyclization of tosylmethyl isocyanide derivatives: total synthesis of mansouramycin B.

Publications > Coppola et al

Org Lett. 2015, 17, 78 PubMed 25521281

Isoquinoline synthesis by heterocyclization of tosylmethyl isocyanide derivatives: total synthesis of mansouramycin B.

Anna Coppola, David Sucunza, Carolina Burgos, Juan J Vaquero

Departamento de Quimica Organica y Quimica Inorganica, Universidad de Alcala , 28871 Alcala de Henares, Madrid, Spain.

Abstract

A new method for the synthesis of isoquinolines through a catalytic acid-mediated cyclization of alpha-benzyl TosMIC derivatives has been developed. This methodology has been successfully applied to the total synthesis of mansouramycin B. This is the first total synthesis of this compound to be reported in the literature.