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.
| 元の言語 | English |
|---|---|
| ページ（範囲） | 5804-5814 |
| ページ数 | 11 |
| ジャーナル | Journal of Organic Chemistry |
| 巻 | 64 |
| 発行部数 | 16 |
| DOI | |
| 出版物ステータス | Published - 1999 8 6 |
| 外部発表 | Yes |
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ASJC Scopus subject areas
- Organic Chemistry
これを引用
Effects of shape on thermodynamic cyclizations of cinchona alkaloids. / Rowan, Stuart J.; Reynolds, Dominic J.; Sanders, Jeremy K M.
：: Journal of Organic Chemistry, 巻 64, 番号 16, 06.08.1999, p. 5804-5814.研究成果: Article
}
TY - JOUR
T1 - Effects of shape on thermodynamic cyclizations of cinchona alkaloids
AU - Rowan, Stuart J.
AU - Reynolds, Dominic J.
AU - Sanders, Jeremy K M
PY - 1999/8/6
Y1 - 1999/8/6
N2 - 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.
AB - 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.
UR - http://www.scopus.com/inward/record.url?scp=0033529893&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=0033529893&partnerID=8YFLogxK
U2 - 10.1021/jo982496x
DO - 10.1021/jo982496x
M3 - Article
AN - SCOPUS:0033529893
VL - 64
SP - 5804
EP - 5814
JO - Journal of Organic Chemistry
JF - Journal of Organic Chemistry
SN - 0022-3263
IS - 16
ER -