Cyanohydrins naturally occurring derivatives

Although the cyanohydrin is an uncommon functional group, linamarin and amygdalin are two naturally occurring cyanohydrin derivatives. Both contain a carbon atom bonded to both an oxygen atom and a cyano group, analogous to a cyanohydrin. 

Naturally occurring cyanohydrin derivatives—linamarin, from cassava root and amygdahn, commonly called laetrile, from apricot, peach and wild cherry pits (Section 21.9B)... 

P,7-Unsaturated ethers of cyanohydrins, on formation of lithio derivatives, undergo a 2,3-sigmatropic rearrangement to form. y-unsaturated ketones (equation 21), whereas benzylic ethers of aliphatic cyanohydrins gave o-methylaryl ketones. The method has been used to prepare 3-methyi-l-(3-methyl-2-furyl)-l-butanones, a naturally occurring Cio terpene, a-allenic ketones and enolic monoethers of 7-keto aldehydes via 2,3-sigmatropic rearrangement of tiieir respective carbanions. ... 

This strategy has been exploited in the synthesis of variety of naturally occurring compounds such as pheromones and steroids." For example, selective elimination of the aeetate moiety from cyanohydrin derivative 95 was used to prepare key intermediate 96. Diene 96 was subsequently elaborated to pellitorine (97). ... 

Cyanohydrins occur naturally, often as derivatives in which the -OH group has been modified to -OR, where R is a carbohydrate unit. These cyanogenic glycosides are widespread in plants one, called amygdaiin, is found in bitter almonds and in the kernels of peaches, plums, apricots, and related fruits. 

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