Disconnection of Carbinols

Abstract A problem-solving approach to retrosynthesis is introduced. Basic principles for good disconnections are postulated. Examples of interconversion and disconnection of carbinols, alkenes, ketones and nitro compounds are discussed. Concepts of retro-Diels-Alder and re/ro-Wittig disconnections are presented and the mechanisms of reactions explained. Application of the Wittig reaction on the industrial scale is exemphfied by the synthesis of the analog of bombykol, the principal of pear odor and anti-appelizer chlorphentermine. 

A problem-solving approach to retrosynthesis is introduced with examples selected according to the functional group that participates in C-C bond disconnection or is interconverted. The key retrosynthetic steps suggest important synthetic reactions, such as Diels-Alder, cyanhydrin, Wittig and Nef reactions. An argumentation is presented for the feasibility of the Wittig reaction on the industrial scale and its acceptability from the environmental aspect. 

The importance of nitroalkanes as building blocks and precursors of prim-amines and ketones is exemplified. 

Retrosyntheses and syntheses of natural and commercial compounds of medium complexity are presented, such as the analog of the pheromone Bombykol, an unsaturated ester principle of pear odor, a key intermediate in the industrial synthesis of P-carotene, and the anti-appetizer chlorphentermine. 

Sunjic and V. Petrovic Perokovic, Organic Chemistry from Retrosynthesis to Asymmetric Synthesis, DOI 10.1007/978-3-319-29926-6 2 

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