Carbenoid Insertion Chemistry on Furanose Platforms as a Route to Natural Product Frameworks

Abstract

The following describes a successful synthetic pathway to create an analog of the natural product (+)-dihydrocanadensolide from the inexpensive and readily available D-xylose. The pathway will describe protecting group chemistry, an esterification, a diazo transfer reaction, and the key step being a metal-catalyzed intramolecular insertion reaction. The metal catalyst used in this step is rhodium(II) acetate and it will be shown to catalyze the decomposition of a diazoester, thus creating a new carbon-carbon bond by carbenoid insertion chemistry. The end result is a bicyclic compound with a fused furan ring system common to many important and useful natural products.