Total synthesis of madindoline A

S. Hosokawa; K. Sekiguchi; K. Hayase; Y. Hirukawa; S. Kobayashi

doi:10.1016/S0040-4039(00)00939-4

Total synthesis of madindoline A

S. Hosokawa, K. Sekiguchi, K. Hayase, Y. Hirukawa, S. Kobayashi^*

^*Corresponding author for this work

Research output: Contribution to journal › Article › peer-review

32 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 language	English
Pages (from-to)	6435-6439
Number of pages	5
Journal	Tetrahedron Letters
Volume	41
Issue number	33
DOIs	https://doi.org/10.1016/S0040-4039(00)00939-4
Publication status	Published - 2000 Aug 12
Externally published	Yes

Keywords

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

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/S0040-4039(00)00939-4

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title = "Total synthesis of madindoline A",

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.",

keywords = "Intramolecular condensation, Madindoline A, Reductive coupling, Tin(II) triflate, Total synthesis",

author = "S. Hosokawa and K. Sekiguchi and K. Hayase and Y. Hirukawa and S. Kobayashi",

note = "Funding Information: We thank Prof. Satoshi Ōmura (Kitasato Institute) for providing NMR spectra of madindoline A and B. We also thank Dr Toshiaki Sunazuka (Kitasato University) for helpful discussions. This work was supported in part by the Fujisawa Foundation (S.H.) and Grant-in-Aid for Scientific Research from the Ministry of Education, Science, Sports, and Culture, Japan.",

year = "2000",

month = aug,

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doi = "10.1016/S0040-4039(00)00939-4",

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volume = "41",

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journal = "Tetrahedron Letters",

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publisher = "Elsevier Limited",

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TY - JOUR

T1 - Total synthesis of madindoline A

AU - Hosokawa, S.

AU - Sekiguchi, K.

AU - Hayase, K.

AU - Hirukawa, Y.

AU - Kobayashi, S.

N1 - Funding Information: We thank Prof. Satoshi Ōmura (Kitasato Institute) for providing NMR spectra of madindoline A and B. We also thank Dr Toshiaki Sunazuka (Kitasato University) for helpful discussions. This work was supported in part by the Fujisawa Foundation (S.H.) and Grant-in-Aid for Scientific Research from the Ministry of Education, Science, Sports, and Culture, Japan.

PY - 2000/8/12

Y1 - 2000/8/12

N2 - 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.

AB - 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.

KW - Intramolecular condensation

KW - Madindoline A

KW - Reductive coupling

KW - Tin(II) triflate

KW - Total synthesis

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DO - 10.1016/S0040-4039(00)00939-4

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SP - 6435

EP - 6439

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 33

ER -

Total synthesis of madindoline A

Abstract

Keywords

ASJC Scopus subject areas

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