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Synthesis 2006(5): 853-859  
DOI: 10.1055/s-2006-926329
PAPER
© Georg Thieme Verlag Stuttgart · New York

A Concise Route for the Synthesis of Biologically Interesting Pyranocoumarins - Seselin, (±)-cis-Khellactone, (±)-Quianhucoumarin D, and the (±)-5-Deoxyprotobruceol-I Regioisomer

Yong Rok Lee*a, Won Kyong Leea, Seok Kyun Noha, Won Seok Lyoob
a School of Chemical Engineering and Technology, Yeungnam University, Gyeongsan 712-749, Korea
b School of Textiles, Yeungnam University, Gyeongsan 712-749, Korea
Fax: +82(53)8104631; e-Mail: yrlee@yu.ac.kr;
Further Information

Publication History

Received 20 July 2005
Publication Date:
07 February 2006 (online)

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Abstract

An efficient synthesis of pyranocoumarins is achieved starting from 2H-pyrans. This process provides naturally occurring seselin, cis-khellactone, quianhucoumarin D, and the 5-deoxyprotobruceol-I regioisomer.

Key words

ring-opening - epoxides - nucleophiles - formylations - pyranocoumarin derivatives

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Spectral data for 31: IR (neat): 3053, 2928, 1651, 1593, 1453, 1412, 1348, 1331, 1302, 1263, 1190, 1163, 1136, 1071, 1020, 920: 864 cm - 1. 1H NMR (300 MHz, CDCl3): δ = 6.44 (1 H, d, J = 10.0 Hz), 5.16 (1 H, d, J = 10.0 Hz), 5.06 (1 H, t, J = 7.1 Hz), 2.40-2.33 (4 H, m), 2.03-1.93 (4 H, m), 1.75-1.68 (2 H, m), 1.65 (3 H, s), 1.54 (3 H, s), 1.34 (3 H, s).