抄録
Thermodynamic cyclizations of a series of cinchona alkaloid derivatives are investigated. An extended quinine monomer 2:HO-Ce-OMe is prepared and cyclized to produce a mixture of cyclic oligomers. Combining the extended monomer 2:HO-Ce-OMe with the previously reported cinchonidine monomer 1b:HO- Cc-OMe under thermodynamic control produces a library of quinine-derived macrocycles. Two quinidine-derived methyl ester monomers 10:HO-Cd-OMe and 16:HO-Ca-OMe are also reported. Both are preorganized to form cyclic dimers; upon carrying out the thermodynamic cyclization on a mixture of both monomers only a small percentage (5%) of the hetero-dimer is obtained. Thermodynamic cyclization of the corresponding cinchonidine derived methyl ester 1b:HO-Cc- OMe with 10:HO-Cd-OMe results in the self-sorting of the two diastereoisomers.
| 本文言語 | English |
|---|---|
| ページ（範囲） | 5804-5814 |
| ページ数 | 11 |
| ジャーナル | Journal of Organic Chemistry |
| 巻 | 64 |
| 号 | 16 |
| DOI | |
| 出版ステータス | Published - 1999 8月 6 |
| 外部発表 | はい |
ASJC Scopus subject areas
- 有機化学