PRINS CYCLIZATION & ITS APPLICATION IN SYNTHESIS OF NATURAL PRODUCTS: Synthesis of Bioactive Natural Products Containing 1,3-Diols - Softcover

Inhaltsangabe

The coupling of an olefin with a carbonyl compound in the presence of an acid catalyst is known as the 'Prins reaction' which normally provides a mixture of 1,3-diols, 1,3-dioxanes, and allylic alcohols. In particular, the coupling of a homoallylic alcohol with a carbonyl compound in the presence of an acid catalyst is known as the 'Prins cyclization', which is a powerful synthetic tool for the stereo selective synthesis of tetrahydropyran scaffolds. On the other hand, aza-Prins cyclization of homoallylic amides with carbonyl compounds is one of the most elegant approaches for the synthesis of piperidine derivatives. In the same way, thia-Prins cyclization of homoallylicmercaptans with aldehydes under the influence of an acid catalyst provides the corresponding thiotetrahydropyrans with a high selectivity. Thus, the Prins cyclization has emerged as a powerful method for the stereo selective synthesis of a wide range of heterocycles such as tetrahydropyran, piperidine and thiotetrahydropyran scaffolds. In this book, we used Prins reaction for synthesis of bioactive natural products such as Polyrhacitide A, Dodoneine, Epi-dodoneine, Euschapholide and Tetraketide.

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