Quassinoid support studies: Fused carbocycle synthesis from benzoic acid derivatives via 5-hexynyl and 6-heptynyl radical cyclizations

Organic Letters

Volumn 8, Issue 20, 2006, Pages 4577-4580

  Cwynar, Valerie ^a   Donahue, Matthew G ^a   Hart, David J ^a   Yang, Dexi ^a  

^a OHIO STATE UNIVERSITY   (United States)

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Indexed keywords

EID: 33750040568     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol061802n     Document Type: Article

References (45)

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33. We thank Dr. Judith Gallucci (OSU) for performing this X-ray cyrstallographic analysis.
34. The ratio of products was determined by NMR spectroscopy of the crude product mixture. The isomers were not completely separated by chromatography, but pure samples of each isomer were obtained (see the Supporting Information).
35. Impure materials that appear to be derived from initial addition of tri-n-butylstannyl radical to the terminal acetylene were also detected.
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37. 2H NMR spectrum deuterated 26.
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42. 2H NMR spectrum of deuterated 33.
43. Alkyne 37 was actually characterized after desilylation to provide 38 (see the Supporting Information).
44. The conversions of 16 to 33 or 36 each require only seven steps and proceed in 9% and 7% overall yields, respectively.
45. 7 diastereomers of cyclization substrates 12, 15, and 25 behave similarly to the substrates described herein.