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Synthesis 2011(19): 3190-3194  
DOI: 10.1055/s-0030-1260177
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Stereoselective Synthesis of Cytotoxic Marine Metabolite Harzialactone A by Three Different Routes [¹]

Duddukuri Nandan Kumar, Cheruku Ravindra Reddy, Biswanath Das*
Organic Chemistry Division-1, Indian Institute of Chemical Technology, Hyderabad 500607, India
Fax: +91(40)27160512; e-Mail: biswanathdas@yahoo.com;
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Publication History

Received 21 June 2011
Publication Date:
18 August 2011 (online)

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Abstract

The cytotoxic marine metabolite harzialactone A has been synthesized stereoselectively starting from phenylacetaldehyde through three different routes. The key steps were: in the first approach Sharpless asymmetric dihydroxylation, in the second approach diastereoselective iodo carbonate preparation, and in the third approach Jacobsen’s hydrolytic kinetic resolution. In all these three schemes the triol was successfully converted into the lactone by using highly chemoselective oxidation with TEMPO and (di­acet­oxyiodo)benzene.

Key words

harzialactone A - stereoselective synthesis - Maruoka allylation - Sharpless asymmetric dihydroxylation - stereoselective iodo carbonate preparation - Jacobsen’s hydrolytic kinetic resolution

1

Part 38 in the series, ‘Synthetic studies on natural products’.

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1

Part 38 in the series, ‘Synthetic studies on natural products’.