Premium
Synthesis of (2 R ,3a R ,8a R )‐6‐Chloro‐3a‐hydroxy‐l,2,3,3a,8,8a‐hexahydropyrrolo[2,3‐ b ]indole‐2‐carboxylic Acid Methyl Ester by Reductive Cyclization
Author(s) -
Hong WenXu,
Yao Zhujun
Publication year - 2004
Publication title -
chinese journal of chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.28
H-Index - 41
eISSN - 1614-7065
pISSN - 1001-604X
DOI - 10.1002/cjoc.20040220410
Subject(s) - chemistry , indole test , reagent , intramolecular force , aldehyde , ring (chemistry) , aldol reaction , carboxylic acid , stereochemistry , combinatorial chemistry , organic chemistry , catalysis
Abstract A synthesis of (2 R ,3a R ,8a R )‐6‐chloro‐3a‐hydroxy‐1,2,3a8,8a‐hexahydropyrrolo[2,3‐ b ]indole‐2‐carboxylic acid methyl ester (1) was achieved. An aldol reaction with Garner aldehyde, a hydroxyl introduction by Davis reagent, and a reductive intramolecular ring‐closure reaction were served as the key steps. This piece of work provides a new way to synthesize the analogues of hexahydropyrrolo[2,3‐b]indole, starting from readily available chemical substrates and inexpensive reagents.