Use of intramolecular [3+ 2] cycloaddition reactions in the synthesis of natural products. A stereospecific synthesis of (.+-.)-biotin from cycloheptene

PN Confalone, ED Lollar, G Pizzolato…

Index: Confalone,P.N. et al. Journal of the American Chemical Society, 1978 , vol. 100, p. 6291 - 6292

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Citation Number: 45

Abstract

Reactions generally classified as 1, 3-dipolar cycloadditions have been extensively employed in the synthesis of a diverse array of heterocyclic compounds. However, this reaction mode has been alloted a more limited role in the preparation of natural products. 2 This is surprising since the cycloadditions are not only ring-forming reactions but also proceed with a high degree of stereo~ electivity.~