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Synthesis of (2R,3aR,8aR)-6-Chloro-3a-hydroxy-l,2,3,3a,8,8a-hexahydropyrrolo[2,3-b]indole-2-carboxylic Acid Methyl Ester by Reductive Cyclization

✍ Scribed by Wen-Xu Hong; Zhujun Yao

Book ID
102804051
Publisher
John Wiley and Sons
Year
2010
Tongue
English
Weight
524 KB
Volume
22
Category
Article
ISSN
0256-7660

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✦ Synopsis

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.

📜 SIMILAR VOLUMES

Encyclopedia of Reagents for Organic Syn
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ChemInform Abstract: Synthesis of the 3a
ChemInform Abstract: Synthesis of the 3a-(3-Indolyl)-1,2,3,3a,8,8a-hexahydropyrrolo[2,3-b]indole Core of Leptosins D—F.
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Synthesis of the 3a-(3-Indolyl)-1,2,3,3a,8,8a-hexahydropyrrolo[2,3b]indole Core of Leptosins D-F. -The Fischer indole reaction of the previously reported L-tryptophan-derived aldehyde (I) with phenyl hydrazine in the presence of freshly fused zinc chloride provides the core unit (IV) of the leptosin

ChemInform Abstract: (2R,3R,5R)-2-[(2R,3
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## Abstract ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable v