Journal of the Korean Chemical Society (대한화학회지)

Korean Chemical Society (대한화학회)
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Synthetic Studies on Discokiolide B

Discokiolide B의 합성에 관한 연구

  • Kim, Hong Seok (Department of Industrial Chemistry, Kyungpook National University) ;
  • Kim, Sang Hwa (Department of Industrial Chemistry, Kyungpook National University) ;
  • Lee, Ju Young (Department of Industrial Chemistry, Kyungpook National University)
  • 김홍석 (경북대학교 공과대학 공업화학과) ;
  • 김상화 (경북대학교 공과대학 공업화학과) ;
  • 이주영 (경북대학교 공과대학 공업화학과)
  • Published : 19961100
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Abstract

A synthesis of the oxazole skeleton of discokiolide B, represented by discokiic acid 1, is described. Aldol condensation of 2[2'-(4-phenyl-3-butenyl)]-1,3-oxazole 4-carboxaldehyde(4a) with lithium enolate of methyl propionate provided the discokiic acid methyl ester. The key intermediate 2[2'-(4-phenyl-3-butenyl)]-1,3-oxazole-4-carboxaldehyde (4a) has been synthesized from the rhodium-catalyzed cycloaddition of diazomalonaldehyde with nitrile. The relative stereochemistry of the 3-hydroxy-2-methylpropanoate unit of discokiic acid was assigned on the basis of $^1H$ and $^{13}C$ NMR data.

해양천연물 Discokiolide B의 옥사졸 골격인 discokiic acid 1을 합성하였다. 2[2'-(4-Phenyl-3-butenyl)]-1, 3-oxazole-4-carboxaldehyde(4a)와 methyl propionate의 리튬 enolate와의 알돌반응으로부터 discokiic acid methyl ester를 합성하였다. 중요한 반응중간체인 2[2'-(4-Phenyl-3-butenyl)]-1, 3-oxazole-4-carboxaldehyde(4a)는 디아조 말론알데히드와 니트릴을 로듐촉매하에서 반응시켜 얻었다. Discokiic acid의 오른쪽 측쇄 부분인 3-hydroxy-2-methyl 프로판산 부분의 상대적인 입체화학을$^1H$와 $^{13}C$ 핵자기공명 데이터에 근거하여 결정하였다.

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