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http://nopr.niscpr.res.in/handle/123456789/16492| Title: | Formal total synthesis of 2-pupukeanone via radical mediated cyclisation of an enyne |
| Authors: | Srikrishna, A Vijaykumar, D Sharma, G V R |
| Issue Date: | Jul-1999 |
| Publisher: | NISCAIR-CSIR, India |
| Abstract: | Diels-Alder reaction of the dienone 12, obtained by C-alkylation of sodium 2,6-dimethylphenoxide, with acrylonitrile and phenyl vinyl sulfones generate the enynes 14 and 17. Tributyltin radical addition to the terminal acetylene in 14 and 17 lead to the vinylstannanes 15 and 18 via 5-exo trig cyclisation of the resulting vinyl radical, which on oxidative cleavage furnishes the isotwistane-diones 16 and 19. Reductive desulfonylation of the diketosulfone 19 furnishes the dione 11, constituting a formal total synthesis of 2-pupukeanone 5 and 2-isocyanopupukeanone 3. |
| Page(s): | 766-770 |
| Appears in Collections: | IJC-B Vol.38B(07) [July 1999] |
Files in This Item:
| File | Description | Size | Format | |
|---|---|---|---|---|
| IJCB 38B(7) 766-770.pdf | 1.14 MB | Adobe PDF | View/Open |
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