Bioinspired synthesis of pentacyclic onocerane triterpenoids

被引：13

作者：

Bartels, Florian ^{[1
]}

Hong, Young J. ^{[2
]}

Ueda, Daijiro ^{[3
]}

Weber, Manuela ^{[1
]}

Sato, Tsutomu ^{[3
]}

Tantillo, Dean J. ^{[2
]}

Christmann, Mathias ^{[1
]}

机构：

[1] Free Univ Berlin, Inst Chem & Biochem, Takustr 3, D-14195 Berlin, Germany

[2] Univ Calif Davis, Dept Chem, Davis, CA 95616 USA

[3] Niigata Univ, Dept Appl Biol Chem, Grad Sch Sci & Technol, Nishi Ku, Ikarashi 2-8050, Niigata 9502181, Japan

来源：

CHEMICAL SCIENCE | 2017年 / 8卷 / 12期

关键词：

BIOMIMETIC TOTAL-SYNTHESIS; ALPHA-ONOCERIN; STEREOSELECTIVE-SYNTHESIS; FERN CONSTITUENTS; NATURAL-PRODUCTS; CYCLIZATION; OXIDATION; ACID; BIOSYNTHESIS; INTERMEDIATE;

D O I：

10.1039/c7sc03903d

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The first chemical synthesis of pentacyclic onocerane triterpenoids has been achieved. A putative biomimetic tricyclization cascade is employed to forge a fused decalin-/oxepane ring system. The synthetic route proceeds to (+)-cupacinoxepin in seven steps and to (+)-onoceranoxide in eight steps in the longest linear sequence, when starting from geranyl chloride and (+)-sclareolide. The bioinspired epoxypolyene cyclization is supported by computational and enzymatic studies.

引用

页码：8285 / 8290

页数：6

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