Unexpected decarbonylation during an acid-mediated cyclization to access the carbocyclic core of zoanthenol
An unusual loss of CO was observed during a key cyclization event in efforts toward the total synthesis of zoanthenol. The synthesis of the cyclization precursor and a proposed mechanism for decarbonylation are detailed.
Additional Information© 2009 Elsevier. Received 17 January 2009; accepted 21 January 2009. Available online 29 January 2009. The authors wish to thank Novartis (predoctoral fellowship to JLS), the Philanthropic Education Organization (Scholar Award to JLS), the John and Fannie Hertz Foundation (predoctoral fellowship to DCB), and Abbott, Amgen, Boehringer-Ingelheim, Bristol-Myers Squibb, Merck, and Caltech for their generous financial support. The authors acknowledge Dr. Andrew McClory for experimental assistance and helpful discussions. Special thanks to Professor Andrew S. Kende for a stimulating discussion regarding the mechanism in Scheme 5. Supplementary data associated with this article can be found, in the online version, at doi:10.1016/j.tetlet.2009.01.121.
Supplemental Material - Stockdillmmc1.pdf