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- W2950455429 abstract "An enantioselective, stereocontrolled total synthesis of eunicenone A (1) is described starting from geranylgeranylacetylene (9) in 14 steps via intermediates 10-20. The most critical construction in the synthesis is the highly effective Diels-Alder combination of the achiral components 2-bromoacrolein and diene 13 in the presence of the chiral Lewis acid catalyst 14 to form 15 (85% yield, 97% ee, >98:2 endo-exo ratio). The synthesis utilizes a novel reagent (12) for introduction of silicon, which serves to activate and direct the diene 13 for Diels-Alder reaction and to provide for eventual oxygen functionality of homoallylic alcohol 17 under mild conditions. Other noteworthy steps include the position selective and diastereoselective epoxidation 17 --> 18, the methoxycarbonylation with allylic transposition 19 --> 20, and the alpha,beta-enone unmasking 20 --> 1." @default.
- W2950455429 created "2019-06-27" @default.
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- W2950455429 date "2010-05-25" @default.
- W2950455429 modified "2023-09-24" @default.
- W2950455429 title "ChemInform Abstract: Enantioselective Total Synthesis of Eunicenone A." @default.
- W2950455429 cites W1966115069 @default.
- W2950455429 doi "https://doi.org/10.1002/chin.200126184" @default.
- W2950455429 hasPublicationYear "2010" @default.
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