Tetrahedron

Synthesis of the 5-hydroxymethyl-6-aryl-8-oxabicyclo [3.2. 1] oct-3-en-2-one natural products descurainin and cartorimine

BB Snider, JF Grabowski

Index: Snider, Barry B.; Grabowski, James F. Tetrahedron, 2006 , vol. 62, # 22 p. 5171 - 5177

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Citation Number: 30

Abstract

Reaction of pyranulose 6 with styrenes 12c or 13 and Et3N in CH2Cl2 at 25° C afforded the [5+ 2] cycloadducts 14c and 15, which were hydrolyzed to give the natural products 1 and descurainin (2) in 24 and 27% overall yield, respectively. Heating pyranulose 6 with cinnamate ester 21 in the presence of 2, 6-di-t-butylpyridine in CH3CN at 175° C afforded the [5+ 2] cycloadduct, which was hydrolyzed to give cartorimine (3) in 13% yield.