Total Synthesis of Highly Oxygenated Bisabolane Sesquiterpene Isolated from Ligularia lankongensis: Relative and Absolute Configurations of the Natural Product

被引：10

作者：

Kobayashi, Kenichi ^{[1
]}

Kunirnura, Risako ^{[1
]}

Takagi, Hirokazu ^{[2
]}

Hirai, Misaki ^{[2
]}

Kogen, Hiroshi ^{[1
]}

Hirota, Hiroshi ^{[3
]}

Kuroda, Chiaki ^{[2
]}

机构：

[1] Meiji Pharmaceut Univ, Grad Sch Pharmaceut Sci, 2-522-1 Noshio, Kiyose, Tokyo 2048588, Japan

[2] Rikkyo Univ, Dept Chem, Toshima Ku, 3-34-1 Nishi Ikebukuro, Tokyo 1718501, Japan

[3] RIKEN CSRS, Chem Genom Res Grp, Wako, Saitama 3510198, Japan

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2018年 / 83卷 / 02期

关键词：

1,3-DIOL ACETONIDES; DIVERSITY; STEREOCHEMISTRY; CHINA; MODEL;

D O I：

10.1021/acs.joc.7b02688

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The relative and absolute configurations of an oxygenated bisabolane natural product, isolated from Ligularia lankongensis, were determined by synthesis. All four possible stereoisomers and their tiglate analogues were synthesized from R(-)-carvone, and their H-1 and C-13 NMR spectra were compared to establish the 6R,8S,10S configuration. The stereoselective synthesis of the natural product was also achieved, featuring Brown allylation, vanadium -catalyzed epoxidation, and the Mitsunobu reaction.

引用

页码：703 / 715

页数：13

共 9 条

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