Total synthesis of madindoline A

Seijiro Hosokawa, K. Sekiguchi, K. Hayase, Y. Hirukawa, S. Kobayashi

Research output: Contribution to journalArticle

29 Citations (Scopus)

Abstract

The total synthesis of madindoline A was achieved. The key step of the synthesis is a reductive coupling of an acid-sensitive hydroxyfuroindoline derivative and a sterically hindered aldehyde using Sn(OTf)2-NaBH(OAc)3. After the reductive coupling, the derived trione was subjected to intramolecular condensation to construct a madindoline skeleton. (C) 2000 Elsevier Science Ltd.

Original languageEnglish
Pages (from-to)6435-6439
Number of pages5
JournalTetrahedron Letters
Volume41
Issue number33
Publication statusPublished - 2000 Aug 12
Externally publishedYes

Fingerprint

Skeleton
Aldehydes
Acids
Condensation
Derivatives
madindoline A

Keywords

  • Intramolecular condensation
  • Madindoline A
  • Reductive coupling
  • Tin(II) triflate
  • Total synthesis

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

Cite this

Hosokawa, S., Sekiguchi, K., Hayase, K., Hirukawa, Y., & Kobayashi, S. (2000). Total synthesis of madindoline A. Tetrahedron Letters, 41(33), 6435-6439.

Total synthesis of madindoline A. / Hosokawa, Seijiro; Sekiguchi, K.; Hayase, K.; Hirukawa, Y.; Kobayashi, S.

In: Tetrahedron Letters, Vol. 41, No. 33, 12.08.2000, p. 6435-6439.

Research output: Contribution to journalArticle

Hosokawa, S, Sekiguchi, K, Hayase, K, Hirukawa, Y & Kobayashi, S 2000, 'Total synthesis of madindoline A', Tetrahedron Letters, vol. 41, no. 33, pp. 6435-6439.
Hosokawa S, Sekiguchi K, Hayase K, Hirukawa Y, Kobayashi S. Total synthesis of madindoline A. Tetrahedron Letters. 2000 Aug 12;41(33):6435-6439.
Hosokawa, Seijiro ; Sekiguchi, K. ; Hayase, K. ; Hirukawa, Y. ; Kobayashi, S. / Total synthesis of madindoline A. In: Tetrahedron Letters. 2000 ; Vol. 41, No. 33. pp. 6435-6439.
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