Synthesis

Synthesis of Siloxy-α-Lapachone Derivatives by Chemo-and Regioselective Diels-Alder Reactions of 3-Methylene-1, 2, 4-naphthotriones with Silyl Enol Ethers

DQ Peng, Y Liu, ZF Lu, YM Shen, JH Xu

Index: Peng, Da-Quan; Liu, Yun; Lu, Zhi-Feng; Shen, Yong-Miao; Xu, Jian-Hua Synthesis, 2008 , # 8 p. 1182 - 1192

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Citation Number: 5

Abstract

Abstract o-Quinone methides, generated in situ from the Knoevenagel condensation of 2- hydroxy-1, 4-naphthoquinone with aliphatic and aromatic aldehydes, take part in chemoselective hetero-Diels-Alder reactions with silyl enol ethers to give a series of siloxy- containing naphtho [2, 3-b] pyran-5, 10-dione (α-lapachone) derivatives in moderate to high yield. These reactions regioselectively gave α-lapachone derivatives with an acetal ...