Synthesis of Protoilludanes and Related Sesquiterpenes

Siengalewicz, Peter; Mulzer, Johann; Rinner, Uwe.

Eur. J. Org. Chem. 2011, (35), 7041-7055.

A review.  Natural products continue to hold the interest and attention of a wide chem. community.  This is due to their biol. properties and potential applicability in health care and plant protection, as well as their frequently complex mol. architectures and arrays of functionality, which make them a challenge for total synthesis and a testing ground for novel methodol.  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 compds.  Biosynthesis, biol. 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 multifaceted picture of the changes in and development of synthetic philosophy and methodol. from past to present.