通过[3+2]环加成立体选择性地形成四氢呋喃环：Plakortone L 的全合成。

Stereoselective formation of tetrahydrofuran rings via [3 + 2] annulation: total synthesis of Plakortone L.

机构信息

Department of Chemistry and Biological Science, Aoyama Gakuin University , 5-10-1, Fuchinobe, Chuo-ku, Sagamihara-shi 252-5258, Japan.

出版信息

Org Lett. 2014 Jun 20;16(12):3384-7. doi: 10.1021/ol501446w. Epub 2014 Jun 4.

DOI:10.1021/ol501446w

PMID:24896660

Abstract

The [3 + 2] annulation of 2,3-O-isopropylidene-aldehydo-aldose with methallyl ether leads to the stereoselective formation of a substituted tetrahydrofuran system, which is converted to a bicyclic lactone derivative via consecutive deprotection, oxidative cleavage of the terminal diol, oxidation of the resulting lactol, and Barton-McCombie deoxygenation. The efficiency of this process was demonstrated by the first total synthesis of Plakortone L.

摘要

[3 + 2] 环加成反应使 2,3-O-异亚丙基-醛糖与甲基烯丙基醚反应，立体选择性地形成取代的四氢呋喃系统，然后通过连续脱保护、末端二醇的氧化裂解、生成的内脂醇的氧化和 Barton-McCombie 脱氧反应转化为双环内酯衍生物。该过程的效率通过 Plakortone L 的首次全合成得到了证明。