Synthesis and Diels-Alder reactions of 1, 3-dimethyl-4-(phenylsulfonyl)-4H-furo [3, 4-b] indole. A new annulation strategy for the construction of ellipticine and …

…, MG Saulnier, MP Sibi, JA Obaza-Nutaitis

Index: Gribble, Gordon W.; Saulnier, Mark G.; Sibi, Mukund P.; Obaza-Nutaitis, Judy A. Journal of Organic Chemistry, 1984 , vol. 49, # 23 p. 4518 - 4523

Full Text: HTML

Citation Number: 116

Abstract

The novel fused heterocycle 1, 3-dimethyl-4-(phenylsulfonyl)-4H-furo [3, 4-b] indole(4) is synthesized from 3-ethylindole (6) in six steps (46% yield) or from indole-3-carboxaldehyde (12) in four steps (21% yield). Furoindole 4 undergoes Diels-Alder reactions with dimethyl acetylenedicarboxylate, N-phenylmaleimide, benzyne, and 3, 4-pyridyne (5) to give the expected adducts 17, 18a, b, 19, and 23a, b, respectively. Deoxygenation and ...

Related Articles:

Total syntheses of ellipticine alkaloids and their amino analogues

[Sha, Chin-Kang; Yang, Jeng-Fenn Tetrahedron, 1992 , vol. 48, # 48 p. 10645 - 10654]

A convenient access to 1, 3-disubstituted furo [3, 4-b] indoles by acid ion-exchange resin-catalyzed furan formation

[Basset, Joan; Romero, Manel; Serra, Thais; Pujol, M. Dolors Tetrahedron, 2012 , vol. 68, # 1 p. 356 - 362]

Improved procedure for the reductive phenylation and cyclization of nitroarenes

[Miyake, Shinji; Sasaki, Atsushi; Ohta, Toshiharu; Shudo, Koichi Tetrahedron Letters, 1985 , vol. 26, # 47 p. 5815 - 5818]

Improved procedure for the reductive phenylation and cyclization of nitroarenes

[Miyake, Shinji; Sasaki, Atsushi; Ohta, Toshiharu; Shudo, Koichi Tetrahedron Letters, 1985 , vol. 26, # 47 p. 5815 - 5818]

Improved procedure for the reductive phenylation and cyclization of nitroarenes

[Miyake, Shinji; Sasaki, Atsushi; Ohta, Toshiharu; Shudo, Koichi Tetrahedron Letters, 1985 , vol. 26, # 47 p. 5815 - 5818]

More Articles...