Abstract
The synthetic aspects of biomimetic cyclizations of isoprenoid polyenes, simulating one of the key steps in the biosynthesis of terpenoids in living organisms, have been reviewed, with emphasis on transformations carried out on carbocyclic systems. These reactions are made possible by a clever choice of initiating and terminating units of cyclization, and by introducing suitable functional groups on the acyclic precursor which can be manipulated after cyclization. Complex functionalized polycyclic structures are thus assembled with an efficiency paralleling or even superior that of purely biochemical processes. In particular, synthetic strategies towards alkyl and hydroxyl-substituted compounds have been examined in detail. The last part of the review has been dedicated to a thorough illustration of carbenium ion initiated polyene cyclizations, with their synthetic applications and a discussion of the different mechanisms proposed.
Keywords: dihydroxylations, cationic cyclizations, Carbocations, Prenylated compounds, Olefin
Current Organic Chemistry
Title: Biomimetic Cyclizations of Functionalized Isoprenoid Polyenes: A Cornucopia of Synthetic Opportunities
Volume: 10 Issue: 17
Author(s): Enrico Brunoldi, Marco Luparia, Alessio Porta, Giuseppe Zanoni and Giovanni Vidari
Affiliation:
Keywords: dihydroxylations, cationic cyclizations, Carbocations, Prenylated compounds, Olefin
Abstract: The synthetic aspects of biomimetic cyclizations of isoprenoid polyenes, simulating one of the key steps in the biosynthesis of terpenoids in living organisms, have been reviewed, with emphasis on transformations carried out on carbocyclic systems. These reactions are made possible by a clever choice of initiating and terminating units of cyclization, and by introducing suitable functional groups on the acyclic precursor which can be manipulated after cyclization. Complex functionalized polycyclic structures are thus assembled with an efficiency paralleling or even superior that of purely biochemical processes. In particular, synthetic strategies towards alkyl and hydroxyl-substituted compounds have been examined in detail. The last part of the review has been dedicated to a thorough illustration of carbenium ion initiated polyene cyclizations, with their synthetic applications and a discussion of the different mechanisms proposed.
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Cite this article as:
Brunoldi Enrico, Luparia Marco, Porta Alessio, Zanoni Giuseppe and Vidari Giovanni, Biomimetic Cyclizations of Functionalized Isoprenoid Polyenes: A Cornucopia of Synthetic Opportunities, Current Organic Chemistry 2006; 10 (17) . https://dx.doi.org/10.2174/138527206778742614
DOI https://dx.doi.org/10.2174/138527206778742614 |
Print ISSN 1385-2728 |
Publisher Name Bentham Science Publisher |
Online ISSN 1875-5348 |
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