Studies toward the construction of the allyltrisulfide Component in esperamicin-A 1 from 5-ketoshikimic acid derivatives: Part 1

Abstract

The conversion of keto ester 1, obtained in either enantiomeric form from (−)-quinic acid, to its corresponding enol silyl ether 4 was examined as the first step to construct the allyl trisulfide unit found in esperamicin A 1. Under different conditions a very facile dimerization of either 4 or enolate 10 to give compound 14 was observed.