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 inCollection of Czechoslovak chemical communications Vol. 64; no. 3; pp. 533 - 538
Main Authors Mane, RB, Kadam, AJ
Format Journal Article
LanguageEnglish
Published PRAGUE 6 Inst Organic Chem And Biochem 1999
Subjects
Chemistry
Chemistry, Multidisciplinary
Physical Sciences
Science & Technology
occidol
Vilsmeier-Haack reaction
sesquiterpenoids
total synthesis
1,2,3,4-tetrahydronaphthalenes
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Abstract 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).
AbstractList 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).
Author Mane, RB
Kadam, AJ
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Keywords occidol
Vilsmeier-Haack reaction
sesquiterpenoids
total synthesis
1,2,3,4-tetrahydronaphthalenes
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Chemistry, Multidisciplinary
Physical Sciences
Science & Technology
Title A new synthesis of occidol
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