Oxoketene dithioacetals as versatile synthons for alternative 1,3 to 1,11 carbonyl transpositions: a new polyene synthesis

Chandrasekharam, Malapaka ; Asokan, Chitoorthekkathil V. ; Ila, Hiriyakkanavar ; Junjappa, Hiriyakkanavar (1990) Oxoketene dithioacetals as versatile synthons for alternative 1,3 to 1,11 carbonyl transpositions: a new polyene synthesis Tetrahedron Letters, 31 (12). pp. 1763-1766. ISSN 0040-4039

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Official URL: http://linkinghub.elsevier.com/retrieve/pii/S00404...

Related URL: http://dx.doi.org/10.1016/S0040-4039(00)88875-9

Abstract

A model strategy for 1,7 to 1,I1 carbonyI transpositions involving 1,2 addition of sodium borohydride or Grignard reagents to polyenyl oxoketene dithioacetals 8 obtained by condensation of bis(methylthio)polyenals 1-3 with active methylene ketones, followed by borontrifluoride etherate catalyzed methanolysis of the resulting polyenyl carbinol acetals 9 to give 1,n transposed polyene esters 10 has been described.

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