Article
Controlling The Radical 5-exo-trig Cyclization, And Selective Synthesis Of Seco-iso-cyclopropylfurano[e]indoline (seco-iso-cfi) And Seco-cyclopropylthiophene[e]indoline (seco-cti) Dna Alkylating Subunit Of The Duocarmycins
Tetrahedron Letters
Document Type
Article
Publication Date
8-28-2013
Publisher
Pergamon-Elsevier Science Ltd
Abstract
The free radical cyclization of benzofuran bromo-allylic chloride 6 in toluene produced an unpredicted mixture of 6-benzyloxy-N-t-Boc-3-(chloromethyl)furano[e]indoline (1) and 7-benzyloxy-N-Boc-3-(chloromethyl)furano[f]quinoline (2). DFT calculations indicated that the indoline radical (6B), formed from 5-exo-trig closure of intermediate 6A, was less polar than the corresponding quinoline radical (6C). Based on this result, we report herein that cyclization of chlorides 6-8 in a polar aromatic solvent consistently and exclusively produced the indoline product in good yield (74-83%). (C) 2013 Elsevier Ltd. All rights reserved.
Keywords
- seco-Cyclopropyltetrahydroquinoline,
- Cc-1065,
- Duocarmycins,
- (chloromethyl)furano[e]indoline,
- (chloromethyl)furano[f]tetrahydroquinoline,
- Biological Evaluation,
- Cc-1065 Analogs,
- Agent,
- CBI,
- C2
Disciplines
Citation Information
Patil, Pravin C., Karalyne Cousins, Mallory Smith, Sarah Wieskamp, Maddi Ferrara, Chrystal D. Bruce and Moses Lee. "Controlling the Radical 5-Exo-Trig Cyclization, and Selective Synthesis of Seco-Iso-Cyclopropylfurano[E]Indoline (Seco-Iso-Cfi) and Seco-Cyclopropylthiophene[E]Indoline (Seco-Cti) Dna Alkylating Subunit of the Duocarmycins." Tetrahedron Letters 54, no. 35 (2013): 4756-4759.