The first total synthesis of hibarimicinone, a potent v-Src tyrosine kinase inhibitor

Kuniaki Tatsuta; Tomohiro Fukuda; Tatsuya Ishimori; Rearu Yachi; Shinpei Yoshida; Hiroshi Hashimoto; Seijiro Hosokawa

doi:10.1016/j.tetlet.2011.11.062

The first total synthesis of hibarimicinone, a potent v-Src tyrosine kinase inhibitor

Kuniaki Tatsuta
, Tomohiro Fukuda
, Tatsuya Ishimori
, Rearu Yachi
, Shinpei Yoshida
, Hiroshi Hashimoto
, Seijiro Hosokawa^*

^*Corresponding author for this work

School of Advanced Science and Engineering

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

25 Citations (Scopus)

Abstract

The first total synthesis of hibarimicinone has been achieved. The polyhydroxydecalin moieties (AB and GH rings) have been synthesized from sulfonylenone 4 derived from d-arabinose. The chiral biaryl 20 was coupled with two polyhydroxydecalins 11 by Michael-Dieckmann type condensation to give the eight rings system. Aromatization and oxidation with Ag ⁺ gave quinone 24, and the subsequential transannular etheration gave the hibarimicinone skeleton. Deprotection and tautomerization were performed in one pot to give hibarimicinone (1).

Original language	English
Pages (from-to)	422-425
Number of pages	4
Journal	Tetrahedron Letters
Volume	53
Issue number	4
DOIs	https://doi.org/10.1016/j.tetlet.2011.11.062
Publication status	Published - 2012 Jan 25

Keywords

Hauser annulation
Hibarimicin
Hibarimicinone
Thiolactone
Total synthesis

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/j.tetlet.2011.11.062

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title = "The first total synthesis of hibarimicinone, a potent v-Src tyrosine kinase inhibitor",

abstract = "The first total synthesis of hibarimicinone has been achieved. The polyhydroxydecalin moieties (AB and GH rings) have been synthesized from sulfonylenone 4 derived from d-arabinose. The chiral biaryl 20 was coupled with two polyhydroxydecalins 11 by Michael-Dieckmann type condensation to give the eight rings system. Aromatization and oxidation with Ag + gave quinone 24, and the subsequential transannular etheration gave the hibarimicinone skeleton. Deprotection and tautomerization were performed in one pot to give hibarimicinone (1).",

keywords = "Hauser annulation, Hibarimicin, Hibarimicinone, Thiolactone, Total synthesis",

author = "Kuniaki Tatsuta and Tomohiro Fukuda and Tatsuya Ishimori and Rearu Yachi and Shinpei Yoshida and Hiroshi Hashimoto and Seijiro Hosokawa",

note = "Funding Information: Authors thank Professor Hiroshi Hori in Tamagawa University, Professor Yasuhiro Igarashi and Professor Tamotsu Furumai in Toyama Prefectural University for providing hibarimicinone and its NMR spectra. Authors are grateful for the financial support to GCOE program {\textquoteleft}Center for Practical Chemical Wisdom{\textquoteright}, and The Ministry of Education, Culture, Sports, Science and Technology (MEXT). ",

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journal = "Tetrahedron Letters",

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AU - Tatsuta, Kuniaki

AU - Fukuda, Tomohiro

AU - Ishimori, Tatsuya

AU - Yachi, Rearu

AU - Yoshida, Shinpei

AU - Hashimoto, Hiroshi

AU - Hosokawa, Seijiro

N1 - Funding Information: Authors thank Professor Hiroshi Hori in Tamagawa University, Professor Yasuhiro Igarashi and Professor Tamotsu Furumai in Toyama Prefectural University for providing hibarimicinone and its NMR spectra. Authors are grateful for the financial support to GCOE program ‘Center for Practical Chemical Wisdom’, and The Ministry of Education, Culture, Sports, Science and Technology (MEXT).

PY - 2012/1/25

Y1 - 2012/1/25

N2 - The first total synthesis of hibarimicinone has been achieved. The polyhydroxydecalin moieties (AB and GH rings) have been synthesized from sulfonylenone 4 derived from d-arabinose. The chiral biaryl 20 was coupled with two polyhydroxydecalins 11 by Michael-Dieckmann type condensation to give the eight rings system. Aromatization and oxidation with Ag + gave quinone 24, and the subsequential transannular etheration gave the hibarimicinone skeleton. Deprotection and tautomerization were performed in one pot to give hibarimicinone (1).

AB - The first total synthesis of hibarimicinone has been achieved. The polyhydroxydecalin moieties (AB and GH rings) have been synthesized from sulfonylenone 4 derived from d-arabinose. The chiral biaryl 20 was coupled with two polyhydroxydecalins 11 by Michael-Dieckmann type condensation to give the eight rings system. Aromatization and oxidation with Ag + gave quinone 24, and the subsequential transannular etheration gave the hibarimicinone skeleton. Deprotection and tautomerization were performed in one pot to give hibarimicinone (1).

KW - Hauser annulation

KW - Hibarimicin

KW - Hibarimicinone

KW - Thiolactone

KW - Total synthesis

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DO - 10.1016/j.tetlet.2011.11.062

M3 - Article

AN - SCOPUS:84155167079

SN - 0040-4039

VL - 53

SP - 422

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JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 4

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The first total synthesis of hibarimicinone, a potent v-Src tyrosine kinase inhibitor

Abstract

Keywords

ASJC Scopus subject areas

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