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UBC Theses and Dissertations

Studies related to the veratrum alkaloids : the total synthesis of C-nor-D-homo steriod analogue Torupka, J. Edward


The total synthesis of trans-syn-cis-C-nor-2-methoxy-8, 11-dihydroxy-10a-methyl-4b,5,6,6a,7,8,9,10,10a,10b,11-undecahydro chrysene (87) is described. This compound has been synthesized from the C-nor-D-homo hydroxy aldehyde (67) via the olefin (71) by oxidative hydroboration. This sequence has the advantage of giving a much higher overall yield of (87). The conversion of the said compound (87), to the a-methyl ketone (74), a relay compound which has been used to synthesize verarine (76) is now nearing completion. Contrary to previous speculations⁸⁸, pyrolidene enamine methylation of model compounds (77,78) did not prove as fruitful as methylation of trapped enolates (figure 13). [diagram omitted]

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