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DOI: 10.1055/s-0042-1753161
Total Synthesis of Pagodane
“Pagodane”: The Efficient Synthesis of a Novel, Versatile Molecular Framework.
J. Am. Chem. Soc. 1987;
109: 4626-4642
DOI: 10.1021/ja00249a029.
Key words
pagodane - Diels–Alder reaction - [2+2] cycloaddition - Brown hydroboration - Wolff rearrangement - Hunsdiecker reaction
Significance
In 1987, Prinzbach and co-workers disclosed the first total synthesis of the undecacyclic strained compound pagodane. Their interest came from the close relationship of pagodane to the entirely pentagonal structure dodecahedrane. Later studies of Prinzbach focused on the synthesis of dodecahedrane and its derivatives from intermediates of the pagodane synthesis.
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Comment
The synthesis of pagodane commences with the Diels–Alder reaction of isodrin A with diene B. Dechlorination followed by a second Diels–Alder reaction affords heptacycle E. Decarbonylation and dehydrogenation results in dibenzo compound G. Its irradiation leads to H via a reversible [2+2] cycloaddition. H is further elaborated into pagodane in nine steps.
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Publication History
Article published online:
16 December 2022
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