Tetrahedron

Tandem reactions of α-diazo ketones with macrocyclic olefins: diastereoselective synthesis of oxanorbornane fused macrocyclic lactones

S Muthusamy, B Gnanaprakasam

Index: Muthusamy, Sengodagounder; Gnanaprakasam, Boopathy Tetrahedron, 2007 , vol. 63, # 16 p. 3355 - 3362

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Citation Number: 13

Abstract

Tandem cyclization–cycloaddition reactions of α-diazo ketones with macrocyclic olefins in the presence of rhodium (II) acetate catalyst led to the oxanorbornane fused macrocyclic di- or tetralactone ring systems in moderate yield. This forms the first example of 1, 3-dipolar cycloaddition reactions with a macrocyclic olefin as a dipolarophile, affording a variety of new oxanorbornane fused macrocycles with diastereoselectivity.