Affiliation:
1. Division of Medicinal and Process Chemistry CSIR-CDRI Lucknow 226031 India
2. Academy of Scientific & Innovative Research (AcSIR) Ghaziabad UP 201002 India
Abstract
AbstractThe discovery of milder and robust strategies to enable the introduction of organoboronates in peptides remains conspicuously underdeveloped. Herein, we demonstrate an efficient method for the site‐selective sp2‐C7−H borylation of tryptophan under metal‐free condition using BBr3 directed by pivaloyl group. The versatility of this approach is that gram scale synthesis and C7‐borylated N‐Phth‐Trp(N‐Piv)(C7‐BPin)‐OMe was modified into various C7‐substituted derivatives. Moreover, the strategy enables for the peptide elongation and late‐stage borylation of peptides, natural product Brevianamide F and drug Oglufanide.
Funder
Central Drug Research Institute
Subject
General Chemistry,Biochemistry,Organic Chemistry
Cited by
4 articles.
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