Chapter 9 - Recent developments in the synthesis of bioactive natural products using Prins-type cyclization

Abstract

The development of novel strategies for natural product synthesis has always been an important goal in organic synthesis. Most of the natural products are the fundamental source of drugs. Among various methods, Prins cyclization has emerged as one of the best ways for the construction of natural products and its analogs. Prins cyclization is a method initially used for the creation of oxygen-containing heterocyclic units. Later on, this is extended to its nitrogen version known as aza-Prins cyclization, which has its own relevance. The fascinating factors of this cyclization are its high diastereoselectivity and single-step construction of carbon–carbon and carbon–heteroatom bonds. The development of its asymmetric version has increased its utility manifolds. Concomitant to other synthetic methods, it has further enhanced the ability to form complex ring moieties present in nature, thus the contribution of Prins cyclization is endless in natural product synthesis. In this chapter, a brief account of the recent (2010 onward) valuable developments in the field of Prins and aza-Prins-mediated cyclization toward natural product synthesis, mostly emphasizing those steps that involve Prins cyclization as the key step is presented. As the scope of the reaction is broad, this review is intended to cover only the synthesis of natural products having oxacyclic and azacyclic moieties. This review may be a useful guide for synthetic organic chemists, especially those who are engaged in natural product synthesis.