Organic Letters 2008-07-17

One-pot synthesis of 2-substituted indoles from 2-aminobenzyl phosphonium salts. A formal total synthesis of arcyriacyanin A.

George A Kraus, Haitao Guo

Index: Org. Lett. 10(14) , 3061-3, (2008)

Full Text: HTML

Abstract

The reaction of (2-aminobenzyl) triphenylphosphonium bromide with aromatic aldehydes or alpha,beta-unsaturated aldehydes under microwave-assisted conditions constitutes a new synthesis of 2-substituted indoles in high yields (81-97%) in a one-pot reaction. The adduct from indole-4-carboxaldehyde was an advanced intermediate in the synthesis of arcyriacyanin A.

Structure	Name/CAS No.	Molecular Formula	Articles
	1H-Indole-4-carbaldehyde CAS:1074-86-8	C₉H₇NO

Synthesis and biological evaluation of achiral indole-substi...
2012-01-01
[Int J Med Chem 2012 , 905981, (2015)]

A New Synthesis method of indole-4-carboxaldehyde. Wu Y-M, e...
[Chinese J. Synth. Chem. 12 , 333-35, (2004)]

Total syntheses of clavine alkaloids by an intramolecular ni...
[Tetrahedron 39(22) , 3695-3705, (1983)]

Synthesis of (-)-chanoclavine I. Kardos N and Genet J-P.
[Tetrahedron Asymmetry 5(8) , 1525-33, (1994)]

Synthesis of Fused 4, 5-Disubstituted Indole Ring Systems by...
[J. Org. Chem. 73(7) , 2920-23, (2008)]

One-pot synthesis of 2-substituted indoles from 2-aminobenzyl phosphonium salts. A formal total synthesis of arcyriacyanin A.

Abstract

Related Compounds