EMAIL THIS PAGE TO A FRIEND

The Journal of organic chemistry

Alternative spiroketalization methods toward purpuromycin: a diketone approach to prevent benzofuran formation.


PMID 21707106

Abstract

The central portion of purpuromycin has been assembled via a classical spiroketalization reaction. Key to promoting this reaction mode versus benzofuran formation was the oxidation state of the spiroketal core. With a higher oxidation state, even the electron-deficient isocoumarin found in purpuromycin could be employed directly in the spiroketalization. The two halves of the spiroketalization precursor were joined via a nitrile oxide/styrene 1,3-dipolar cycloaddition. A very mild selenium dioxide oxidation was used to introduce the required oxidation state of the spiroketal core.

Related Materials

Product #

Image

Description

Molecular Formula

Add to Cart

B8002
2,3-Benzofuran, 99%
C8H6O