A New Synthesis of Occidol

[img]PDF - Authorized users only
Language: English
66Kb
Title:A New Synthesis of Occidol
Creators:
Mane, Ramchandra Bhimrao
Kadam, Abhijit Jaysingrao
Journal or Publication Title:
Collection of Czechoslovak Chemical Communications, 64, 3, pp. 533-538
Uncontrolled Keywords:Sesquiterpenoids, Total synthesis, Occidol, 1,2,3,4-Tetrahydronaphthalenes, Vilsmeier-Haack reaction

Abstract

Sodium borohydride reduction of 5,8-dimethyl-3,4-dihydronaphthalen-1-(2<i>H</i>)-one (<strong>4</strong>) yielded 5,8-dimethyl-1,2,3,4-tetrahydro-1-naphthol (<strong>5</strong>). The tetralol <strong>5</strong> on Vilsmeier-Haack reaction with <i>N,N</i>-dimethylacetamide yielded 1-(5,8-dimethyl-3,4-dihydro-2-naphthyl)ethan-1-one (<strong>7</strong>) which on hydrogenation over Pd/C afforded 1-(5,8-dimethyl-1,2,3,4-tetrahydro-2-naphthyl)ethan-1-one (<strong>8</strong>). The tetralol <strong>5</strong> on Vilsmeier-Haack formylation gave 5,8-dimethyl-3,4-dihydro-2-naphthaldehyde (<strong>9</strong>) 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 (<strong>11</strong>). The acid <strong>11</strong> on treatment with excess of methyllithium yielded (±)-occidol (<strong>1</strong>); with two moles of methyllithium it yielded ketone <strong>8</strong>, which on reaction with methyllithium furnished (±)-occidol (<strong>1</strong>). <p>

Title:A New Synthesis of Occidol
Creators:
Mane, Ramchandra Bhimrao
Kadam, Abhijit Jaysingrao
Uncontrolled Keywords:Sesquiterpenoids, Total synthesis, Occidol, 1,2,3,4-Tetrahydronaphthalenes, Vilsmeier-Haack reaction
Divisions:Life and Chemical Sciences > Institute of Organic Chemistry and Biochemistry > Collection of Czechoslovak Chemical Communications
Journal or Publication Title:Collection of Czechoslovak Chemical Communications
Volume:64
Number:3
Page Range:pp. 533-538
ISSN:0010-0765
E-ISSN:1212-6950
Publisher:Institute of Organic Chemistry and Biochemistry
Related URLs:
URLURL Type
http://dx.doi.org/10.1135/cccc19990533UNSPECIFIED
ID Code:1495
Item Type:Article
Deposited On:06 Feb 2009 17:10
Last Modified:06 Feb 2009 16:10

Citation

Mane, Ramchandra Bhimrao; Kadam, Abhijit Jaysingrao (1999) A New Synthesis of Occidol. Collection of Czechoslovak Chemical Communications, 64 (3). pp. 533-538. ISSN 0010-0765

Repository Staff Only: item control page