Journal article
Synthesis of the Zoanthamine ABC Ring System: Some Surprises from Intramolecular Diels-Alder Reactions
[reaction: see text] In connection with the total synthesis of the marine alkaloids zoanthamine and norzoanthamine, an elaborate model study was conducted starting from (-)-carvone. In nine steps alkenyl iodides corresponding to the C11-C24 fragment of zoanthamine were obtained. The alkenyl iodides were coupled to various stannanes (C6-C10 fragment) via the Corey modification of the Stille reaction, affording a variety of Diels-Alder precursors.
An interesting and highly unexpected cascade reaction sequence was observed during the screening of an intramolecular Diels-Alder reaction, generating a novel tetracyclic framework. A slight modification in the Diels-Alder precursor allowed the desired cycloaddition to take place, giving the cycloadduct in 87% yield.
Language: | English |
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Year: | 2006 |
Pages: | 265-280 |
ISSN: | 15206904 and 00223263 |
Types: | Journal article |
DOI: | 10.1021/jo0520691 |
ORCIDs: | Tanner, David Ackland |