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The Aza‐Prins Reaction in the Synthesis of Natural Products and Analogues
Author(s) -
Subba Reddy B. V.,
Nair Preethi Narayanan,
Antony Aneesh,
Lalli Claudia,
Grée René
Publication year - 2017
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201601411
Subject(s) - prins reaction , natural product , total synthesis , chemistry , pyran , organic synthesis , biochemical engineering , organic chemistry , combinatorial chemistry , catalysis , engineering
The classical Prins cyclization reaction has been one of the most studied reactions during the last two decades and it has found many applications in key steps of natural product syntheses, especially for products containing pyran units and related structures in their core skeletons. The nitrogen‐based version of the Prins reaction, aza‐Prins cyclization, has found its own relevance in organic synthesis owing to the fact that it gives direct access to piperidines, which are even more widespread in natural products and in drugs. Even though the potential scope of the reaction is vast, and despite it having afforded significant progress in the synthesis of various azaheterocycles, its applications in the field of natural product synthesis is massively underdeveloped in comparison with the classical Prins reaction. A compilation of the applications of aza‐Prins cyclization in the preparation of natural products and selected analogues, especially compounds of potential biological interest, is presented, with emphasis placed on the key roles of this reaction in the total synthesis of these products.