Synthesis of the central tricyclic core of the isatisine A: harmonious orchestration of [metal]-catalyzed reactions in a sequence

TitleSynthesis of the central tricyclic core of the isatisine A: harmonious orchestration of [metal]-catalyzed reactions in a sequence
Publication TypeJournal Article
Year of Publication2014
AuthorsPatel, P, B. Reddy, N, Ramana, CV
JournalTetrahedron
Volume70
Issue2
Pagination510-516
Date PublishedJAN
ISSN0040-4020
KeywordsDehydrogenative cyclization, Friedel-Crafts reaction, Indium chloride, Isatisine A, Rhodium, Spiro-3-indolinone
Abstract

Two sequential metal-catalyzed transformations, involving [In]-catalyzed Friedel Crafts type addition of spiroaminol carbon to indole C3 followed by [Rh]-catalyzed dehydrogenative cyclization of the resulting gamma-amino alcohol culminated in the construction of the central tricyclic core isatisine A. The overall strategy employed three easily available starting compounds and delivered the complex tricyclic core in four steps with all four steps being catalytic in nature. (C) 2013 Elsevier Ltd. All rights reserved.

DOI10.1016/j.tet.2013.11.026
Type of Journal (Indian or Foreign)Foreign
Impact Factor (IF)2.641
Divison category: 
Organic Chemistry