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A Model Study toward the Synthesis of Xestoquinone

Xestoquinone의 합성에 대한 모델연구

  • Ahn Chan Mug (Department of Basic Science, Institute of Basic Medical Science, Yonsei University Wonju College of Medicine) ;
  • Ho Bum Woo (Department of Basic Science, Institute of Basic Medical Science, Yonsei University Wonju College of Medicine)
  • 안찬묵 (연세대학교 원주의과대학 기초과학교실) ;
  • 우호범 (연세대학교 원주의과대학 기초과학교실)
  • Published : 2003.08.20

Abstract

A strategy for synthesis of the furan-fused tetracyclic system of xestoquinone was explored through a model study. Using 3-butyn-1-ol as a starting material, 5-iodo-1-methoxymethoxy pentyne (5) was prepared in 5 steps. Reaction of ethyl 2-phenylpropanoate with 5 gave ethyl 7-methoxymethoxy-2-methyl-2-phenyl-5-heptynoate (6) in 88% yield, and then methyl 9-oxo-4-methyl-4-phenyl-2,7-nonadiynoate (13), the key intermediate, was synthesized in 6 steps from the ester 6. Intramolecular cycloaddition reaction of 13 afforded isobenzofuran 14 in 5% yield, which was converted to the tetracyclic structure 15 in the presence of Lewis acid.

Keywords

Xestoguinone;Intramolecular;Cycloaddition

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Cited by

  1. Strategies for the Synthesis of the Halenaquinol and Xestoquinol Families of Natural Products vol.2017, pp.12, 2017, https://doi.org/10.1002/ejoc.201601418