隣接位に酸素官能基を有するビシナルジブロミドの脱離反応を利用した生物活性天然物の全合成研究 [in Japanese] Synthetic Studies on Bioactive Natural Products Utilizing the Elimination Reaction of 1,2-Dibromides Possessing Oxygen-Functional Groups at Adjacent Positions [in Japanese]
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2-Bromo-1-alkenes have been recognized as one of useful functional groups for preparation of vinyl lithiums and vinyl Grignard reagents, for coupling partners in a wide range of transition metal-mediated coupling reactions, substrates of radical reactions, and precursors of a-haloke-tones. Selective elimination reaction of 1, 2-dibromoalkanes possessing aryloxy or acyloxy groups at the C 3 position into 2-bromo-1-alkenes under mild basic conditions was developed. Alkyne units are also one of the important functional groups for substrates of C-C coupling reactions. During our extensive investigation, the acidity enhancement of hydrogen at the C 1 position by oxygen-functional groups at the C 3 position was also observed. This observation indicated a new prospective synthesis of propargyl ethers from 1, 2-dibromoalkanes using DBU as a base. As application of these elimination reactions, total synthesis of biologically active natural products was accomplished.
- J. Synth. Org. Chem. Jpn.
J. Synth. Org. Chem. Jpn. 66(2), 139-147, 2008-02-01
The Society of Synthetic Organic Chemistry, Japan