The Total Synthesis of Eleutherobin
详细信息 查看全文
- 作者：Xiao-Tao Chen ; Samit K. Bhattacharya ; Bishan Zhou ; Clare E. Gutteridge ; Thomas R. R. Pettus ; and Samuel J. Danishefsky
- 刊名：Journal of the American Chemical Society
- 出版年：1999
- 出版时间：July 21, 1999
- 年：1999
- 卷：121
- 期：28
- 页码：6563 - 6579
- 全文大小：494K
- 年卷期：v.121,no.28(July 21, 1999)
- ISSN：1520-5126
文摘
The total synthesis of the title compound (1), starting with (R)-(-)-
-phellandrene (6), has beenaccomplished. The synthesis rigorously proves the relative stereochemical relationship of the diterpenoid andcarbohydrate domains of eleutherobin. Key reactions included a Nozaki-Kishi ring closure to produce afuranophane (see 37 
38), a pyranose to furanose transposition (see 50 47), and a novel oxycarbaglycosidation (cf. 58 87) for joining the two domains.
-phellandrene (6), has beenaccomplished. The synthesis rigorously proves the relative stereochemical relationship of the diterpenoid andcarbohydrate domains of eleutherobin. Key reactions included a Nozaki-Kishi ring closure to produce afuranophane (see 37 38), a pyranose to furanose transposition (see 50 47), and a novel oxycarbaglycosidation (cf. 58 87) for joining the two domains.