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Synthesis 2011(15): 2437-2440  
DOI: 10.1055/s-0030-1260081
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

A Simple Stereoselective Synthesis of a Novel Cytotoxic Alkaloid Barrenazine A [¹]

Biswanath Das*, Gandham Satyalakshmi, Kanaparthy Suneel
Organic Chemistry Division-1, Indian Institute of Chemical Technology, Hyderabad 500007, India
Fax: +91(40)27160512; e-Mail: biswanathdas@yahoo.Com;
Further Information

Publication History

Received 30 March 2011
Publication Date:
21 June 2011 (online)

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Abstract

The cytotoxic marine alkaloid barrenazine A was synthesized stereoselectively in eight simple steps from octanal. A key step involved the preparation of a functionalized 4- aminopiperidin-5-ol that underwent oxidative dimerization on treatment with 2-iodoxybenzoic acid.

Keywords

alkaloids - stereoselective synthesis - dimerizations - cytotoxins

1

Part 47 in the series Synthetic Studies on Natural Products.

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1

Part 47 in the series Synthetic Studies on Natural Products.