The synthesis of carbocyclic eight-membered rings

Progress in the construction of cyclooctanoid systems: new approaches and applications to natural product syntheses.

Catalysis and synthesis are intimately linked in modern organic chemistry. The synthesis of complex molecules is an ever evolving area of science. In many regards, the inherent beauty associated with a synthetic sequence can be linked to a certain combination of the creativity with which a sequence is designed and the overall efficiency with which the ultimate process is performed. In synthesis, as in other endeavors, beauty is very much in the eyes of the beholder.† It is with this in mind that we will attempt to review an area of synthesis that has fascinated us and that we find extraordinarily beautiful, namely the combination of catalysis and sigmatropic rearrangements in consecutive and cascade sequences.

Toward a Symphony of Reactivity: Cascades Involving Catalysis and Sigmatropic Rearrangements

Convergent Strategies in Total Syntheses of Complex Terpenoids

This article surveys variants of the Claisen rearrangement that are of general use in stereoselective organic synthesis. Recent results concerning the influence of steric and electronic parameters on transition state geometries are highlighted. The impact of the Claisen methodology in modern synthetic strategy and its application for the preparation of highly functionalized derivatives is exemplified.

7.2 – Claisen Rearrangements

Enantioselective synthesis of the complete dicyclopenta[a,d]cyclooctane array represented by the sesterterpene (+)-ceroplastol-I from optically pure keto ketal:tetrahydro 7'a-methylspiro[1,3-dioxolane-2,1'-inden-5'(4'H)-one]

Vo Nha Huu

Papers

Access to naturally occurring cyclooctanoids by two-carbon intercalation. Total synthesis of (+)-ceroplastol I

Two-carbon intercalation. 4-Cyclooctenones by tandem application of double-Tebbe and Claisen reactions