[8+2] cycloaddition reactions of 2H-cyclohepata[b]furan-2-one with acyclic 1,3-dienes: A faculty route to novel bicyclo [5.3.0] ring systems

Tetrahedron Letters

Volumn 38, Issue 36, 1997, Pages 6441-6444

  Nair, Vijay ^a   Anilkumar, G ^a   Nandakumar, M V ^a   Mathew, Bini ^a   Rath, Nigam P ^b  

^a REGIONAL RESEARCH LABORATORY CSIR   (India)

^b UNIVERSITY OF MISSOURI ST LOUIS   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CYCLOHEPTA[B]FURAN DERIVATIVE; CYCLOHEPTANE DERIVATIVE; POLYCYCLIC HYDROCARBON; UNCLASSIFIED DRUG;

ARTICLE; CHIRALITY; DRUG SYNTHESIS; IN VITRO STUDY; METHODOLOGY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0030879774     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)01472-X     Document Type: Article

References (24)

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21. Typical experimental procedure: A solution of 3-ethoxycarbonyl-2H-cyclohepta[b]- furan-2-one (0.218 g, 1 mmol) and 2,3-dimethylbutadiene (0.410 g, 5 mmol) in dry toluene (0.5 mL) was sealed under argon in a Schlenk glass tube and heated at 150°C for 14 h. The reaction mixture was subjected to chromatography on a silica gel column (1% ethyl acetate-hexane) to afford 3 (0.175 g, 97%) as a blood red viscous liquid. The unreacted furanone (0.064 g) was recovered using 30% ethyl acetate-hexane as the eluent.
22. 2: 256.14633; Found: 256.14628.
23. The details of the X-ray analysis will be published separately.
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