A non-tetradecarboxylative synthesis of 2,7,12,17-tetraphenylporphycene
Ana Gavalda
Grup d'Enginyeria Molecular, Institut Químic de Sarrià, Universitat Ramon Llull, Via Augusta, 390, E-08017 Barcelona, Spain
Search for more papers by this authorJosÉ I. Borrell
Grup d'Enginyeria Molecular, Institut Químic de Sarrià, Universitat Ramon Llull, Via Augusta, 390, E-08017 Barcelona, Spain
Search for more papers by this authorJordi Teixido
Grup d'Enginyeria Molecular, Institut Químic de Sarrià, Universitat Ramon Llull, Via Augusta, 390, E-08017 Barcelona, Spain
Search for more papers by this authorCorresponding Author
Santiago Nonell
Grup d'Enginyeria Molecular, Institut Químic de Sarrià, Universitat Ramon Llull, Via Augusta, 390, E-08017 Barcelona, Spain
Grup d'Enginyeria Molecular, Institut Químic de Sarrià, Universitat Ramon Llull, Via Augusta, 390, E-08017 Barcelona, SpainSearch for more papers by this authorOfir Arad
Grup d'Enginyeria Molecular, Institut Químic de Sarrià, Universitat Ramon Llull, Via Augusta, 390, E-08017 Barcelona, Spain
Search for more papers by this authorRoser Grau
Grup d'Enginyeria Molecular, Institut Químic de Sarrià, Universitat Ramon Llull, Via Augusta, 390, E-08017 Barcelona, Spain
Search for more papers by this authorMagdalena CaÑete
Departamento de Biología, Facultad de Ciencias, Universidad Autónoma de Madrid, Cantoblanco, E-28049 Madrid, Spain
Search for more papers by this authorAngeles Juarranz
Departamento de Biología, Facultad de Ciencias, Universidad Autónoma de Madrid, Cantoblanco, E-28049 Madrid, Spain
Search for more papers by this authorAngeles Villanueva
Departamento de Biología, Facultad de Ciencias, Universidad Autónoma de Madrid, Cantoblanco, E-28049 Madrid, Spain
Search for more papers by this authorJuan C. Stockert
Departamento de Biología, Facultad de Ciencias, Universidad Autónoma de Madrid, Cantoblanco, E-28049 Madrid, Spain
Search for more papers by this authorAna Gavalda
Grup d'Enginyeria Molecular, Institut Químic de Sarrià, Universitat Ramon Llull, Via Augusta, 390, E-08017 Barcelona, Spain
Search for more papers by this authorJosÉ I. Borrell
Grup d'Enginyeria Molecular, Institut Químic de Sarrià, Universitat Ramon Llull, Via Augusta, 390, E-08017 Barcelona, Spain
Search for more papers by this authorJordi Teixido
Grup d'Enginyeria Molecular, Institut Químic de Sarrià, Universitat Ramon Llull, Via Augusta, 390, E-08017 Barcelona, Spain
Search for more papers by this authorCorresponding Author
Santiago Nonell
Grup d'Enginyeria Molecular, Institut Químic de Sarrià, Universitat Ramon Llull, Via Augusta, 390, E-08017 Barcelona, Spain
Grup d'Enginyeria Molecular, Institut Químic de Sarrià, Universitat Ramon Llull, Via Augusta, 390, E-08017 Barcelona, SpainSearch for more papers by this authorOfir Arad
Grup d'Enginyeria Molecular, Institut Químic de Sarrià, Universitat Ramon Llull, Via Augusta, 390, E-08017 Barcelona, Spain
Search for more papers by this authorRoser Grau
Grup d'Enginyeria Molecular, Institut Químic de Sarrià, Universitat Ramon Llull, Via Augusta, 390, E-08017 Barcelona, Spain
Search for more papers by this authorMagdalena CaÑete
Departamento de Biología, Facultad de Ciencias, Universidad Autónoma de Madrid, Cantoblanco, E-28049 Madrid, Spain
Search for more papers by this authorAngeles Juarranz
Departamento de Biología, Facultad de Ciencias, Universidad Autónoma de Madrid, Cantoblanco, E-28049 Madrid, Spain
Search for more papers by this authorAngeles Villanueva
Departamento de Biología, Facultad de Ciencias, Universidad Autónoma de Madrid, Cantoblanco, E-28049 Madrid, Spain
Search for more papers by this authorJuan C. Stockert
Departamento de Biología, Facultad de Ciencias, Universidad Autónoma de Madrid, Cantoblanco, E-28049 Madrid, Spain
Search for more papers by this authorAbstract
A new synthetic method for 2,7,12,17-tetraphenylporphycene (2e, TPPo) which avoids tetradecarboxylation by sublimation of the intermediate tetracarboxylic acid 8 is reported. Thus, the use of a pyrrol 13a bearing two orthogonal ester groups allows the synthesis of bipyrrol 12a, from which the benzyl ester groups are selectively removed to afford diester 11. The latter is transformed to dialdehyde 10 by using the McFayden–Stevens reaction, thus avoiding the unstable bipyrrol 9 formed during the tetradecarboxylation of 8. Copyright © 2001 John Wiley & Sons, Ltd.
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