Computer-assisted design and lactonization of model seco-acid derivatives of lankanolide
- 作者：Hamada ; Tatsuo ; Kiyokawa ; Mitsugu ; Kobayashi ; Yukinari ; Yoshioka ; Toshikazu ; Sano ; Junichiro ; et. al.
- 关键词：Conformation calculation ; seco-Acid ; Lactonization ; Lankanolide
- 刊名：Tetrahedron
- 出版年：2004
- 期刊代码：107_00404020
- 类别：ch
- 出版时间：May 17, 2004
- 卷：60
- 期：21
- 页码：4693-4704
- 文件大小：591 K
摘要
In some cases, seco-acid derivatives (a precursor of macrolactone) did not cyclize to form the corresponding macrolactone. To design easily cyclizable seco-acid derivatives of lanaknolide, the conformation of several model seco-acids was calculated, and lactonization experiments of the seco-acids prepared from oleandomycin were carried out to elucidate the efficiency of the cyclization of the model seco-acid. The easily cyclable seco-acid was designed to be C8 exomethylene derivative of lankanolide seco-acid. On the other hand, seco-acid derivative having tertiary alcohol at C8 was predicted not to cyclize to form macrolactone.