Total Synthesis and Structural Revision of Clavilactone D

Ken Ichi Takao; Ryuichi Nemoto; Kento Mori; Ayumi Namba; Keisuke Yoshida; Akihiro Ogura

doi:10.1002/chem.201700483

Total Synthesis and Structural Revision of Clavilactone D

Ken Ichi Takao, Ryuichi Nemoto, Kento Mori, Ayumi Namba, Keisuke Yoshida, Akihiro Ogura

Department of Applied Chemistry

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

17 Citations (Scopus)

Abstract

A structural revision of clavilactone D, a potent inhibitor of protein tyrosine kinases, was achieved by total syntheses of two newly proposed structures. The syntheses relied on ring-opening/ring-closing metathesis, which transformed a cyclobutenecarboxylate into a γ-butenolide. The syntheses confirmed that the correct structure of clavilactone D has an amino group at C-3 instead of a hydroxy group at C-2 in the originally proposed structure.

Original language	English
Pages (from-to)	3828-3831
Number of pages	4
Journal	Chemistry - A European Journal
Volume	23
Issue number	16
DOIs	https://doi.org/10.1002/chem.201700483
Publication status	Published - 2017 Mar 17

Keywords

medium-ring compounds
metathesis
natural products
structure elucidation
total synthesis

ASJC Scopus subject areas

Catalysis
Organic Chemistry

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10.1002/chem.201700483

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title = "Total Synthesis and Structural Revision of Clavilactone D",

abstract = "A structural revision of clavilactone D, a potent inhibitor of protein tyrosine kinases, was achieved by total syntheses of two newly proposed structures. The syntheses relied on ring-opening/ring-closing metathesis, which transformed a cyclobutenecarboxylate into a γ-butenolide. The syntheses confirmed that the correct structure of clavilactone D has an amino group at C-3 instead of a hydroxy group at C-2 in the originally proposed structure.",

keywords = "medium-ring compounds, metathesis, natural products, structure elucidation, total synthesis",

author = "Takao, {Ken Ichi} and Ryuichi Nemoto and Kento Mori and Ayumi Namba and Keisuke Yoshida and Akihiro Ogura",

note = "Funding Information: We thank Professor L. Scaglioni (Universit{\`a} di Milano) for providing the original NMR spectra of clavilactone D. This work was supported by JSPS KAKENHI Grant Number 15K05504 and the Asahi Glass Foundation. Publisher Copyright: {\textcopyright} 2017 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim",

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T1 - Total Synthesis and Structural Revision of Clavilactone D

AU - Takao, Ken Ichi

AU - Nemoto, Ryuichi

AU - Mori, Kento

AU - Namba, Ayumi

AU - Yoshida, Keisuke

AU - Ogura, Akihiro

N1 - Funding Information: We thank Professor L. Scaglioni (Università di Milano) for providing the original NMR spectra of clavilactone D. This work was supported by JSPS KAKENHI Grant Number 15K05504 and the Asahi Glass Foundation. Publisher Copyright: © 2017 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim

PY - 2017/3/17

Y1 - 2017/3/17

N2 - A structural revision of clavilactone D, a potent inhibitor of protein tyrosine kinases, was achieved by total syntheses of two newly proposed structures. The syntheses relied on ring-opening/ring-closing metathesis, which transformed a cyclobutenecarboxylate into a γ-butenolide. The syntheses confirmed that the correct structure of clavilactone D has an amino group at C-3 instead of a hydroxy group at C-2 in the originally proposed structure.

AB - A structural revision of clavilactone D, a potent inhibitor of protein tyrosine kinases, was achieved by total syntheses of two newly proposed structures. The syntheses relied on ring-opening/ring-closing metathesis, which transformed a cyclobutenecarboxylate into a γ-butenolide. The syntheses confirmed that the correct structure of clavilactone D has an amino group at C-3 instead of a hydroxy group at C-2 in the originally proposed structure.

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KW - natural products

KW - structure elucidation

KW - total synthesis

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Total Synthesis and Structural Revision of Clavilactone D

Abstract

Keywords

ASJC Scopus subject areas

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