Singlet oxygen cycloaddition to dienes: A biomimetic approach to marine endoperoxides?

Synlett

Volumn , Issue 9, 1999, Pages 1359-1362

  Harwood, L M ^a   Robertson, J ^a   Swallow, S ^b  

^a UNIVERSITY OF READING   (United Kingdom)

^b ROCHE PRODUCTS LTD   (United Kingdom)

Author keywords

4 + 2 cycloaddition; Ene reaction; Marine endoperoxide; Mycaperoxide; Singlet oxygen

Indexed keywords

ALKADIENE; ENDOPEROXIDE; MYCAPEROXIDE; SESTERTERPENE; SINGLET OXYGEN; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; REACTION ANALYSIS; SPONGE (PORIFERA); SYNTHESIS;

EID: 0032844911     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1999-2851     Document Type: Article

References (23)

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14. Typical experimental procedure: A solution of the diene (0.5 mmol) and tetraphenylporphyrin (25 mg, 40 μmol) in anhydrous dichloromethane (50 mL), was cooled to -78°C and agitated by a constant stream of dry oxygen. The solution was irradiated at -78 °C with a 125 W high pressure mercury lamp for 30-80 minutes, monitoring by TLC analysis. Upon warming the solution to room temperature, and concentration in vacuo, the residue was purified by gradient flash column chromatography on silica, eluting with petrol-ether, increasing the ether, to furnish the oxidation product as an oil.
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21. Zwitterionic or pre-epoxide species have been proposed as intermediates in singlet oxygen cycloadditions: T. Linker and L. Frölich, Angew. Chem. Int. Ed. Engl. 1994, 33, 1971; T. Linker and L. Frölich, J. Am. Chem. Soc. 1995, 117, 2694; T. Linker, F. Rebein and G. Tóth, J. C. S., Chem Commun. 1996, 2585.
22. Zwitterionic or pre-epoxide species have been proposed as intermediates in singlet oxygen cycloadditions: T. Linker and L. Frölich, Angew. Chem. Int. Ed. Engl. 1994, 33, 1971; T. Linker and L. Frölich, J. Am. Chem. Soc. 1995, 117, 2694; T. Linker, F. Rebein and G. Tóth, J. C. S., Chem Commun. 1996, 2585.
23. Zwitterionic or pre-epoxide species have been proposed as intermediates in singlet oxygen cycloadditions: T. Linker and L. Frölich, Angew. Chem. Int. Ed. Engl. 1994, 33, 1971; T. Linker and L. Frölich, J. Am. Chem. Soc. 1995, 117, 2694; T. Linker, F. Rebein and G. Tóth, J. C. S., Chem Commun. 1996, 2585.