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Synthesis 2010(11): 1763-1765  
DOI: 10.1055/s-0029-1219761
SHORTPAPER
© Georg Thieme Verlag Stuttgart ˙ New York

The First Total Synthesis of Racemic 3,4-Dihydroxy-2-(3-methylbut-2-enyl)-3,4-dihydronaphthalen-1(2H)-one

Vangaru Suresh, Jondass Jon Paul Selvam, Karuturi Rajesh, Vanam Shekhar, Dokuburra Chanti Babu, Yenamandra Venkateswarlu*
Organic Chemistry Division-I, Natural Products Laboratory, Indian Institute of Chemical Technology, Hyderabad 500007, India
Fax: +91(40)27160512; e-Mail: luchem@iict.res.in;
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Publikationsverlauf

Received 19 February 2010
Publikationsdatum:
06. April 2010 (online)

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Abstract

Racemic 3,4-dihydroxy-2-(3-methylbut-2-enyl)-3,4-dihydronaphthalen-1(2H)-one is synthesized for the first time, in seven steps, starting from commercially available α-tetralone. The key steps in this process are dihydroxylation using osmium tetroxide, benzylic oxidation mediated by sodium chlorite-tert-butyl hydro­peroxide, and prenylation.

Key words

racemic - natural products - dihydroxylation - benzylic oxidation - prenylation