Synthesis of substituted tetrahydrofuranones and tetrahydropyranones: Photocycloaddition/fragmentation reactions of dioxinones

Tetrahedron Letters

Volumn 38, Issue 32, 1997, Pages 5579-5582

  Dritz, Jay H ^a   Carreira, Erick M ^a  

^a CALIFORNIA INSTITUTE OF TECHNOLOGY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

TETRAHYDROFURAN DERIVATIVE; TETRAHYDROPYRAN DERIVATIVE;

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

EID: 0030750430     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)01262-8     Document Type: Article

References (26)

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3. (c) Winkler, J. D.; Bowen, C. M.; Liotta, F. Chem. Rev. 1995, 95, 2003.
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15. For related work involving the stereoselective [2+2]-photocycloadditions of chiral allenes, see: (a) Carreira, E. M.; Hastings, C. A.; Shepard, M. S.; Yerkey, L. A.; Millward, D. B. J. Am. Chem. Soc. 1994, 116, 6622.
16. (b) Shepard, M. S.; Carreira, E. M. J. Am. Chem. Soc. 1997, 119, 2597.
17. (a) For a recent review in the synthesis of tetrahydropyrans and tetrahydrofurans, see: Alvarez, E.; Candenas, M.-L.; Pérez, R.; Ravelo, J. L.; Martín, J. D. Chem Rev. 1995, 95, 1953.
18. (b) Evans, P. A.; Roseman, J. D. J. Org. Chem. 1996, 61, 2252.
19. For early work on the photocycloaddition of 2,2,6-trimethyl-4H-1,3-dioxin-4-one with alkenes, see: Baldwin, S. W.; Wilkinson, J. M. J. Am. Chem. Soc. 1980, 102, 3634.
20. Winkler has reported an application of the dioxinone photocycloaddition reaction involving the [2+2]-photocycloaddition of vinylogous amide with a dioxinone as an approach to the synthesis of perhydrohistrionicotoxin, see: ref 4b and 4c.
21. All compounds described were prepared in racemic form.
22. Schwesinger, R.; Schlemper, H. Angew. Chem., Ind. Ed. Engl. 1987, 26, 1167.
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25. With the exception of 22, these diastereomers could be separated by chromatography on silica gel.
26. The preference for an axial alkyne (31a) in dioxanes, under equilibrating conditions, has been discussed: Bailey, W. F.; Eliel, E. L. J. Am. Chem. Soc. 1974, 96, 1798.