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Synthesis 2009(7): 1175-1179  
DOI: 10.1055/s-0028-1087998
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

The First Total Synthesis of Kynapcin-24 by Palladium Catalysis

Ling-Yi Yanga, Chia-Fu Changa, Yu-Chao Huanga, Yean-Jang Lee*a, Chao-Chin Hub, Tsui-Hwa Tsengb
a Department of Chemistry, National Changhua University of Education, Changhua 50058, Taiwan
Fax: +886(4)7211190; e-Mail: leeyj@cc.ncue.edu.tw;
b School of Applied Chemistry, Chung Shan Medical University, No. 110, Section 1, Chien-Kuo N. Road, Taichung 402, Taiwan
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Publication History

Received 11 November 2008
Publication Date:
06 March 2009 (online)

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Abstract

The synthesis of kynapcin-24, which can be isolated from the Korean mushroom Polyozellus multiflex Murr, is achieved in 12% overall yield from commercially available 3,4-dihydroxybenzaldehyde by a route in which the longest linear sequence is only 14 steps. The key transformations in the synthesis are copper-mediated and palladium-catalyzed coupling reactions of the iodide 3-iodo-5,6-diisopropoxy-2-[(tetrahydropyran-2-yloxy)methyl]benzofuran with the corresponding stannane 5,6-diisopropoxy-2-[(tetrahydropyran-2-yloxy)methyl]-3-(tributylstannyl)benzofuran, and a 5-endo-dig iodocyclization of a (hydroxyphenyl)propargyl ether.

Key words

kynapcin-24 - copper-mediated - palladium-catalyzed - coupling - cyclizations

15

The X-ray data for 17 have been deposited at CCDC under the number CCDC701406.