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] / Science, Faculty of / Chemistry, Department of / Graduate
| Identifer | oai:union.ndltd.org:UBC/oai:circle.library.ubc.ca:2429/36010 |
| Date | January 1968 |
| Creators | Torupka, J. Edward |
| Publisher | University of British Columbia |
| Source Sets | University of British Columbia |
| Language | English |
| Detected Language | English |
| Type | Text, Thesis/Dissertation |
| Rights | For non-commercial purposes only, such as research, private study and education. Additional conditions apply, see Terms of Use https://open.library.ubc.ca/terms_of_use. |
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