Prasad, Kavirayani R. ; Gholap, Shivajirao L. (2008) Stereoselective total synthesis of bioactive styryllactones (+)-goniofufurone, (+)7-epi-goniofufurone, (+)-goniopypyrone, (+)-goniotriol, (+)-altholactone, and (-)-etharvensin The Journal of Organic Chemistry, 73 (1). pp. 2-11. ISSN 0022-3263
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Official URL: http://pubs.acs.org/doi/abs/10.1021/jo0702342
Related URL: http://dx.doi.org/10.1021/jo0702342
Abstract
Stereoselective total synthesis of biologically active styryllactones 7-epi-goniofufurone, goniofufurone, goniopypyrone, goniotriol, altholactone, and etharvensin was achieved in high overall yields from a common intermediate derived from D-(−)-tartaric acid. It is based on the utility of a masked tetrol, comprising an alkene tether and four contiguous hydroxy groups. The pivotal reaction sequence involves hydroxy-directed lactonization via the oxidation of alkene, and subsequent elaboration to styryllactones. The masked tetrol was prepared by the extension of γ-phenyl-γ-hydroxy butyramide, readily obtained from the bis-dimethylamide of tartaric acid, employing a combination of selective Grignard additions and a stereoselective reduction.
Item Type: | Article |
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Source: | Copyright of this article belongs to American Chemical Society. |
ID Code: | 105794 |
Deposited On: | 21 Dec 2017 12:02 |
Last Modified: | 21 Dec 2017 12:02 |
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