A concise stereoselective synthesis of the C-aromatic taxane skeleton: an application of novel sequential transacetalation oxonium ene cyclization

Sonawane, H. R. ; Maji, D. K. ; Jana, G. H. ; Pandey, G. (1998) A concise stereoselective synthesis of the C-aromatic taxane skeleton: an application of novel sequential transacetalation oxonium ene cyclization Chemical Communications (16). pp. 1773-1774. ISSN 1359-7345

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Official URL: http://pubs.rsc.org/en/content/articlelanding/1998...

Related URL: http://dx.doi.org/10.1039/A804084B

Abstract

A three-step sequence for the construction of the C-aromatic taxane nucleus from easily available A-ring unit 2 and C-aromatic unit 3 is reported; SnCl4 promoted reaction of 4, presumably via the diastereoselective oxonium ene cyclisation reaction of 6a formed in situ, delivers cyclic ether 5a which on treatment with BunLi provides C-aromatic taxane skeleton 8.

Item Type:Article
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