Tetrahedron

Efficient entry to 1-benzoxepine ring skeleton via tandem SN 2/Wittig reaction. Total synthesis of NADH: ubiquinone oxidoreductase (complex I) antagonist pterulinic …

YL Lin, HS Kuo, YW Wang, ST Huang

Index: Lin, Yuh-Lin; Kuo, Hsien-Shou; Wang, Yi-Wen; Huang, Sheng-Tung Tetrahedron, 2003 , vol. 59, # 8 p. 1277 - 1281

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Citation Number: 16

Abstract

Concise synthesis of NADH: ubiquinone oxidoreductase (complex I) antagonist pterulinic acid (1a) is reported. The key architectural framework in the natural product, 1-benzoxepine ring skeleton, was smoothly prepared from known salicylaldehyde 2g and phosphorane 3 via tandem SN2/Wittig reaction. Pterulinic acid was prepared in 5 steps from 2g with overall yield of 25%. The versatility of tandem SN2/Wittig reaction was investigated. This tandem ...