A cyclopropane fragmentation approach to heterocycle assembly: A convergent synthesis of oxepanes

Organic Letters

Volumn 7, Issue 3, 2005, Pages 515-517

  O'Neil, Kerry E ^a   Kingree, Seth V ^a   Minbiole, Kevin P C ^a  

^a JAMES MADISON UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ACETAL DERIVATIVE; ALCOHOL DERIVATIVE; ALUMINUM DERIVATIVE; CYCLOPROPANE DERIVATIVE; HETEROCYCLIC COMPOUND; OXEPANE DERIVATIVE; TITANIUM DERIVATIVE;

ADDITION REACTION; ARTICLE; CHEMICAL REACTION; FRAGMENTATION REACTION; SUBSTITUTION REACTION;

EID: 13844276142     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol047426t     Document Type: Article

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11. 4).
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13. 2) effected formation of acetal 11, though no further reaction was observed.
14. Cis relative stereochemistry of both 11 and 12 was confirmed by one-dimensional NOE analysis. In both cases, irradiation of the benzylic proton led to significant enhancement (∼10%) of the other carbinol proton resonance.
15. 2 = Ph).
16. Deliberate addition of triflic acid did not effect condensation or rearrangement.
17. Spiro compound 34 was not observed in the absence of an aldehyde.
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