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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
Abstract
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]
Item Metadata
| Title |
Studies related to the veratrum alkaloids : the total synthesis of C-nor-D-homo steriod analogue
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| Creator | |
| Publisher |
University of British Columbia
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| Date Issued |
1968
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| Description |
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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| Genre | |
| Type | |
| Language |
eng
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| Date Available |
2011-07-15
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| Provider |
Vancouver : University of British Columbia Library
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| 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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| DOI |
10.14288/1.0061887
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| URI | |
| Degree (Theses) | |
| Program (Theses) | |
| Affiliation | |
| Degree Grantor |
University of British Columbia
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| Campus | |
| Scholarly Level |
Graduate
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| Aggregated Source Repository |
DSpace
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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.