Intermolecular radical cation Diels-Alder (RCDA) reaction of bicyclooctadienes: Biomimetic formal total synthesis of kingianin A and total syntheses of kingianins D, F, H, and J

Journal of Organic Chemistry

Volumn 79, Issue 3, 2014, Pages 919-926

  Lim, Hee Nam ^a   Parker, Kathlyn A ^a  

^a STONY BROOK UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

BICYCLO COMPOUNDS; CATIONS; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; CYCLOADDITION REACTION; MOLECULAR STRUCTURE; POLYCYCLIC HYDROCARBONS, AROMATIC; STEREOISOMERISM;

EID: 84893874084     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo402082y     Document Type: Article

References (13)

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4. However, the authors did see interconversion of monomers 2 and 3; see: Sharma, P.; Ritson, D. J.; Burnley, J.; Moses, J. E. Chem. Commun. 2011, 47, 10605-10607
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6. Lim, H. N.; Parker, K. A. Org. Lett. 2013, 15, 398-401
7. During the preparation of this manuscript, the synthesis of kingianins A, D, and F by a sequence that used the intermolecular RCDA reaction appeared. This work focused primarily on testing the biomimetic premise and it relies on preparative HPLC for the isolation of the individual kingianins. Yields for the recovered kingianins from the HPLC experiment were not reported. See: Drew, S. L.; Lawrence, A. L.; Sherburn, M. S. Angew. Chem., Int. Ed. 2013, 52, 4221-4224
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10. For a related reaction, see: Shukla, P.; Hsu, Y.-C.; Cheng, C.-H. J. Org. Chem. 2006, 71, 655-658
11. For related transformations and a discussion of mechanism, see: Shrestha, R.; Dorn, S. C. M.; Weix, D. J. J. Am. Chem. Soc. 2013, 135, 751-762
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