1993年7月
SYNTHETIC STUDIES ON MACROPYRROLIZIDINE ALKALOID, MONOCROTALINE - ENANTIOSELECTIVE SYNTHESIS OF A NECIC ACID MOIETY, MONOCROTALIC ACID METHYLENE ACETAL
JOURNAL OF ORGANIC CHEMISTRY
- ,
- ,
- 巻
- 58
- 号
- 16
- 開始ページ
- 4274
- 終了ページ
- 4279
- 記述言語
- 英語
- 掲載種別
- DOI
- 10.1021/jo00068a022
- 出版者・発行元
- AMER CHEMICAL SOC
A methylene acetal derivative 4 of the necic acid, monocrotalic acid, part of the macropyrrolizidine alkaloid, monocrotaline, was enantioselectively synthesized from 2-furylmethanol derivative 6. Oxidation of 6, followed by silylation of the resulting lactol 9, gave silyl ether 19 as a major product. Introduction of the di-tert-hydroxy groups to 22 was achieved by stereoselective dihydroxylation with osmium tetroxide. After protection of the vicinal diol as a methylenedioxy derivative, acetal 26 was successfully converted into the desired product 4.
- リンク情報
- ID情報
-
- DOI : 10.1021/jo00068a022
- ISSN : 0022-3263
- CiNii Articles ID : 80007188523
- Web of Science ID : WOS:A1993LV42500022