A novel sulfonamide non-classical carbenoid: a mechanistic study for the synthesis of enediynes-Reference-Cited by-同舟云学术

A novel sulfonamide non-classical carbenoid: a mechanistic study for the synthesis of enediynes

Published:2017 Issue:46 Volume:15 Page:9895-9902
ISSN:1477-0520
Container-title:Organic & Biomolecular Chemistry
language:en
Short-container-title:Org. Biomol. Chem.

Author:

Hayes Theodore O. P.¹²³⁴^ORCID,Slater Ben¹²³⁴^ORCID,Horan Richard A. J.⁵⁶⁷⁴,Radigois Marc¹²³⁴^ORCID,Wilden Jonathan D.¹²³⁴^ORCID

Affiliation:

1. Department of Chemistry

2. University College London

3. London WC1H 0AJ

4. UK

5. GlaxoSmithkline

6. Medicines Research Centre

7. Stevenage

Abstract

Alkynyl sulfonamides undergo sequential 1,4- then 1,2-addition/rearrangement with lithium acetylides to yield enediynes in the absence of any promoters or catalysts. Mechanistic investigations suggest that the reaction proceeds via a novel electrophilic carbenoid with distinct reactivity compared to those previously described.

Funder

Engineering and Physical Sciences Research Council

GlaxoSmithKline

Publisher

Royal Society of Chemistry (RSC)

Subject

Organic Chemistry,Physical and Theoretical Chemistry,Biochemistry

Link

http://pubs.rsc.org/en/content/articlepdf/2017/OB/C7OB02437A

Reference32 articles.

1. The Enediyne Antibiotics

2. Enediyne compounds - new promises in anticancer therapy