Synlett 2004(2): 0306-0310  
DOI: 10.1055/s-2003-44990
LETTER
© Georg Thieme Verlag Stuttgart · New York

Diastereoselective Synthesis of Chiral [4.4]- and [4.5]-Spiroketals from Furan Derivatives: Study on the Asymmetric Synthesis of Tonghaosu Analogs

Biao-Lin Yin, Tai-Shan Hu, Hui-Juan Yue, Yang Gao, Wen-Min Wu, Yu-Lin Wu*
State Key Laboratory of Bio-Organic & Natural Products Chemistry Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 354 Fenglin Road, Shanghai 200032, P. R. China
e-Mail: ylwu@mail.sioc.ac.cn;
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Publication History

Received 21 November 2003
Publication Date:
16 December 2003 (online)

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Abstract

Diastereoselective syntheses of [4.4]- and [4.5]-spiro­ketal featured tonghaosu analogs were explored. An excellent dia­stereoselectivity was achieved for [4.5]-spiroketals due to anomeric, steric, and perhaps π-π interactions; [4.4]-spiroketal could be obtained in good diastereoselectivity by tuning substituted pattern of the tetrahydrofuran ring.