Bromohydrin reactions of Grieco's bicyclic lactone

Tetrahedron Letters

Volumn 49, Issue 48, 2008, Pages 6853-6855

  Tello Aburto, Rodolfo ^a   Rios, Maria Yolanda ^a   Swenson, Dale C ^b   Olivo, Horacio F ^a  

^a UNIVERSITY OF IOWA   (United States)

^b E11 SSH   (United States)

Author keywords

Bromohydrin; Grieco's lactone

Indexed keywords

BROMINE DERIVATIVE; LACTONE;

ARTICLE; X RAY DIFFRACTION;

EID: 53549126617     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2008.09.081     Document Type: Article

References (24)

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15. 3) m/z 250.0028, found m/z 250.0039.
16. CCDC for compound 2: 699517. CCDC for compound 5: 699492. CCDC for compound 8: 699544. CCDC for compound 19: 700139. The CCDC numbers contain the supplementary crystallographic data for this Letter. These data can be obtained free of charge via http://www.ccdc.cam.ac.uk/data_request/cif, by e-mailing to data_request@ccdc.cam.ac.uk contacting the Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge CB2 1EZ, UK, fax: +44 1223 336033.
17. 2).
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23. 3) m/z 140.0473, found m/z 140.0469.
24. We epoxidized bicyclic lactone 1 with m-CPBA. Epoxidation of bicyclic lactone 1 furnished endo- and exo-epoxides 19 and 20 in a 2:1 ratio in 92% overall yield. These two epoxides were separated by column chromatography.{A figure is presented}