A new synthesis of occidol
Sodium borohydride reduction of 5,8-dimethyl-3,4-dihydronaphthalen-1-(2H)-one (4) yielded 5,8-dimethyl-1,2,3,4-tetrahydro-1-naphthol (5). The tetralol 5 on Vilsmeier-Haack reaction with N,N-dimethylacetamide yielded 1-(5,8-dimethyl-3,4-dihydro-2-naphthyl)ethan-1-one (7) which on hydrogenation over P...
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Published in | Collection of Czechoslovak chemical communications Vol. 64; no. 3; pp. 533 - 538 |
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Main Authors | , |
Format | Journal Article |
Language | English |
Published |
PRAGUE 6
Inst Organic Chem And Biochem
1999
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Subjects | |
Online Access | Get more information |
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Summary: | Sodium borohydride reduction of 5,8-dimethyl-3,4-dihydronaphthalen-1-(2H)-one (4) yielded 5,8-dimethyl-1,2,3,4-tetrahydro-1-naphthol (5). The tetralol 5 on Vilsmeier-Haack reaction with N,N-dimethylacetamide yielded 1-(5,8-dimethyl-3,4-dihydro-2-naphthyl)ethan-1-one (7) which on hydrogenation over Pd/C afforded 1-(5,8-dimethyl-1,2,3,4-tetrahydro-2-naphthyl)ethan-1-one (8). The tetralol 5 on Vilsmeier-Haack formylation gave 5,8-dimethyl-3,4-dihydro-2-naphthaldehyde (9) which on reduction with lithium aluminium hydride followed by oxidation with the Jones reagent furnished 5,8-dimethyl-1,2,3,4-tetrahydro-2-naphthoic acid (11). The acid 11 on treatment with excess of methyllithium yielded (+/-)-occidol (1); with two moles of methyllithium it yielded ketone 8, which on reaction with methyllithium furnished (+/-)-occidol (1). |
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ISSN: | 0010-0765 |
DOI: | 10.1135/cccc19990533 |