Silver(I)-Catalyzed Dearomatization of Alkyne-Tethered Indoles: Divergent Synthesis of Spirocyclic Indolenines and Carbazoles

Michael J James; Rosa E Clubley; Kleopas Y Palate; Thomas J Procter; Anthony C Wyton; Peter O'Brien; Richard J K Taylor; William P Unsworth

doi:10.1021/acs.orglett.5b02216

Silver(I)-Catalyzed Dearomatization of Alkyne-Tethered Indoles: Divergent Synthesis of Spirocyclic Indolenines and Carbazoles

Org Lett. 2015 Sep 4;17(17):4372-5. doi: 10.1021/acs.orglett.5b02216. Epub 2015 Aug 21.

Authors

Michael J James¹, Rosa E Clubley¹, Kleopas Y Palate¹, Thomas J Procter¹, Anthony C Wyton¹, Peter O'Brien¹, Richard J K Taylor¹, William P Unsworth¹

Affiliation

¹ Department of Chemistry, University of York , Heslington, York, YO10 5DD, U.K.

PMID: 26293968
DOI: 10.1021/acs.orglett.5b02216

Abstract

A high-yielding, divergent approach to generate either spirocyclic indolenines or carbazoles from a common indole-tethered propargyl alcohol precursor is described, with mechanistic insight provided. Either product can be obtained upon treatment with different Ag(I) catalysts at rt. An unexpected hydration reaction to afford (±)-actinopolymorphol B is also reported.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Alkynes / chemistry
Biological Products / chemical synthesis*
Biological Products / chemistry
Carbazoles / chemical synthesis*
Carbazoles / chemistry
Catalysis
Cyclization
Indole Alkaloids / chemical synthesis*
Indole Alkaloids / chemistry
Molecular Structure
Propanols / chemistry
Silver Nitrate / chemistry
Stereoisomerism

Substances

Alkynes
Biological Products
Carbazoles
Indole Alkaloids
Propanols
actinopolymorphol B
Silver Nitrate
propargyl alcohol