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

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

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...

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Veröffentlicht in:Organic letters 2004-02, Vol.6 (4), p.553-556
Hauptverfasser: Suzuki, Takahiro, Usui, Kenji, Miyake, Yoshiharu, Namikoshi, Michio, Nakada, Masahisa
Format: Artikel
Sprache:eng
Schlagworte:
Antineoplastic Agents - chemical synthesis
Ascomycota - chemistry
Catalysis
Cyclization
Indicators and Reagents
Molecular Structure
Oxidation-Reduction
Pentanoic Acids - chemical synthesis
Stereoisomerism
Tetrahydronaphthalenes - chemical synthesis
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Zusammenfassung: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.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol036338q