First Total Synthesis of Antimitotic Compound, (+)-Phomopsidin

Takahiro Suzuki; Kenji Usui; Yoshiharu Miyake; Michio Namikoshi; Masahisa Nakada

doi:10.1021/ol036338q

First Total Synthesis of Antimitotic Compound, (+)-Phomopsidin

Takahiro Suzuki, Kenji Usui, Yoshiharu Miyake, Michio Namikoshi, Masahisa Nakada^*

^*Corresponding author for this work

School of Advanced Science and Engineering

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

40 Citations (Scopus)

Abstract

(Equation presented) The first total synthesis of (+)-phomopsidin has been achieved via a diastereoselective transannular Diels-Alder (TADA) reaction. Key steps in the synthesis include diastereoselective ynone reduction with (-)-α-pinene and 9-BBN, macrocyclization by E-selective intramolecular Horner-Wadsworth-Emmons (HWE) reaction, as well as carbometalation under Wipf's conditions, followed by HWE reaction at low temperature to selectively construct the (E)-1-methylpropenyl and (1E,2E)-4-carboxy-1,3-butadienyl substituents.

Original language	English
Pages (from-to)	553-556
Number of pages	4
Journal	Organic Letters
Volume	6
Issue number	4
DOIs	https://doi.org/10.1021/ol036338q
Publication status	Published - 2004 Feb 19

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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title = "First Total Synthesis of Antimitotic Compound, (+)-Phomopsidin",

abstract = "(Equation presented) The first total synthesis of (+)-phomopsidin has been achieved via a diastereoselective transannular Diels-Alder (TADA) reaction. Key steps in the synthesis include diastereoselective ynone reduction with (-)-α-pinene and 9-BBN, macrocyclization by E-selective intramolecular Horner-Wadsworth-Emmons (HWE) reaction, as well as carbometalation under Wipf's conditions, followed by HWE reaction at low temperature to selectively construct the (E)-1-methylpropenyl and (1E,2E)-4-carboxy-1,3-butadienyl substituents.",

author = "Takahiro Suzuki and Kenji Usui and Yoshiharu Miyake and Michio Namikoshi and Masahisa Nakada",

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doi = "10.1021/ol036338q",

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T1 - First Total Synthesis of Antimitotic Compound, (+)-Phomopsidin

AU - Suzuki, Takahiro

AU - Usui, Kenji

AU - Miyake, Yoshiharu

AU - Namikoshi, Michio

AU - Nakada, Masahisa

PY - 2004/2/19

Y1 - 2004/2/19

N2 - (Equation presented) The first total synthesis of (+)-phomopsidin has been achieved via a diastereoselective transannular Diels-Alder (TADA) reaction. Key steps in the synthesis include diastereoselective ynone reduction with (-)-α-pinene and 9-BBN, macrocyclization by E-selective intramolecular Horner-Wadsworth-Emmons (HWE) reaction, as well as carbometalation under Wipf's conditions, followed by HWE reaction at low temperature to selectively construct the (E)-1-methylpropenyl and (1E,2E)-4-carboxy-1,3-butadienyl substituents.

AB - (Equation presented) The first total synthesis of (+)-phomopsidin has been achieved via a diastereoselective transannular Diels-Alder (TADA) reaction. Key steps in the synthesis include diastereoselective ynone reduction with (-)-α-pinene and 9-BBN, macrocyclization by E-selective intramolecular Horner-Wadsworth-Emmons (HWE) reaction, as well as carbometalation under Wipf's conditions, followed by HWE reaction at low temperature to selectively construct the (E)-1-methylpropenyl and (1E,2E)-4-carboxy-1,3-butadienyl substituents.

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First Total Synthesis of Antimitotic Compound, (+)-Phomopsidin

Abstract

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