Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 55, Issue 8, Pages 2851-2855Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201510568
Keywords
arenes; diterpenoids; electrocyclization; radical reactions; total synthesis
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Funding
- Ministry of Science Technology [2013CB836900]
- National Natural Science Foundation of China [21525209, 21290180, 21172235, 21222202]
- Shanghai Science and Technology Commission [15JC1400400]
- China Postdoctoral Science Foundation [2014M551480, 2015T80470]
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The total syntheses of ileabethoxazole, pseudopteroxazole, and seco-pseudopteroxazole, three antituberculosis diterpenoids that had been isolated from Pseudopterogorgia elisabethae, were accomplished in a collective fashion. A cascade alkyne carbopalladation/Stille reaction was exploited to construct a triene precursor with suitable geometry. A fully substituted arene was then assembled through a key 6 pi electrocyclization/aromatization sequence, and served as an advanced common intermediate. Two radical cyclizations led to the formation of the five- and six-membered rings of ileabethoxazole and pseudopteroxazole, respectively, with the desired stereochemistry, and a straightforward side-chain elongation delivered seco-pseudopteroxazole.
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