高等学校化学学报

高等学校化学学报 ›› 1998, Vol. 19 ›› Issue (S1): 9.

• Plenary, Keynote and Invited Lectures • 上一篇    下一篇

Recent Progress in the Synthetic Applications of Substituted Furans and Pyrroles

Henry N. C. Wong   

  1. Department of Chemistry, The Chinese University of Hong Kong, Shatin, New Territories, Hong Kong
  • 出版日期:1998-12-31 发布日期:1998-12-31

Recent Progress in the Synthetic Applications of Substituted Furans and Pyrroles

Henry N. C. Wong   

  1. Department of Chemistry, The Chinese University of Hong Kong, Shatin, New Territories, Hong Kong
  • Online:1998-12-31 Published:1998-12-31

PDF (PC)

摘要： In this lecture, I would like to present efficient synthetic routes towards the total synthesis of syringolide 1 (2)1,2 and secosyrin 1 (3),1 employing 2,4-disubstituted furan 1 as a common precursor. A modified total synthesis of prehispanolone (6)3 from (S)-(+)-Wieland-Miescher ketone (4) via hispanolone (5) will also be discussed. Our methodology for the synthesis of 3,4-disubstituted-lH-pyrroles4 and for the generation of 3,4-didehydrothiophene5 has also guided us to the successful identification of 1-tert-butoxycarbonyl-3,4-didehydro-1H-pyrrole (7),which is presumably the most strained heterocyclic cumulene ever recorded.

Abstract: In this lecture, I would like to present efficient synthetic routes towards the total synthesis of syringolide 1 (2)1,2 and secosyrin 1 (3),1 employing 2,4-disubstituted furan 1 as a common precursor. A modified total synthesis of prehispanolone (6)3 from (S)-(+)-Wieland-Miescher ketone (4) via hispanolone (5) will also be discussed. Our methodology for the synthesis of 3,4-disubstituted-lH-pyrroles4 and for the generation of 3,4-didehydrothiophene5 has also guided us to the successful identification of 1-tert-butoxycarbonyl-3,4-didehydro-1H-pyrrole (7),which is presumably the most strained heterocyclic cumulene ever recorded.

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