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Synthesis of Protoilludanes and Related Sesquiterpenes
Author(s) -
Siengalewicz Peter,
Mulzer Johann,
Rinner Uwe
Publication year - 2011
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.201101220
Subject(s) - variety (cybernetics) , chemistry , biochemical engineering , nanotechnology , computer science , engineering , artificial intelligence , materials science
Natural products continue to hold the interest and attention of a wide chemical community. This is due to their biological properties and potential applicability in health care and plant protection, as well as their frequently complex molecular architectures and arrays of functionality, which make them a challenge for total synthesis and a testing ground for novel methodology. These criteria are met to an extraordinary degree by protoilludanes, which are sesquiterpenes with a characteristic tricyclic 5/6/4‐framework. The fortieth anniversary of the first protoilludane synthesis has now been taken as an occasion to review the main aspects of this fascinating class of compounds. Biosynthesis, biological properties and the unusually rich variety of synthetic approaches developed over the past forty years are discussed. About 80 different substitution patterns and 15 completed or uncompleted synthetic routes are listed in this review with the goal of providing a multifacetted picture of the changes in and development of synthetic philosophy and methodology from past to present.