Organic letters

Facile construction of novel polycyclic ring systems using a metallocarbenoid-induced cyclization of acetylenic diazo carbonyl compounds

A Padwa, CS Straub

Index: Padwa, Albert; Straub, Christopher S. Organic Letters, 2000 , vol. 2, # 14 p. 2093 - 2095

Full Text: HTML

Citation Number: 18

Abstract

The Rh (II)-catalyzed reaction of diazo 2-propynyl maolonamic acid ester derivatives produce furo [3, 4-c] furans in excellent yield. The methodology was applied to the synthesis of several polyheterocyclic systems by first generating a 2-alkoxy-substituted furan and then allowing it to undergo a subsequent intramolecular Diels-Alder cycloaddition. Ring opening of the resulting cycloadduct is followed by deprotonation to furnish a rearranged keto ...