New Pathways in Transannular Cyclization of Germacrone [Germacra-1(10),4,7(11)-trien-8-one]: Evidence Regarding a Concerted Mechanism

被引：19

作者：

Barrero, Alejandro F. ^{[1
]}

Mar Herrador, M. ^{[1
]}

Lopez-Perez, Jose-Luis ^{[2
]}

Arteaga, Jesus F. ^{[3
]}

Catalan, Julieta ^{[1
]}

机构：

[1] Univ Granada, Inst Biotechnol, Dept Organ Chem, E-18071 Granada, Spain

[2] Univ Salamanca, Fac Pharm, Dept Pharmaceut Chem, Salamanca 37071, Spain

[3] Univ Huelva, Fac Expt Sci, Dept Chem Engn Phys Chem & Organ Chem, Huelva 21071, Spain

来源：

ORGANIC LETTERS | 2009年 / 11卷 / 21期

关键词：

STEREOSELECTIVE EPOXIDATION; ORGANIC-SYNTHESIS; BIOSYNTHESIS; SESQUITERPENES; DERIVATIVES; CATION; NMR;

D O I：

10.1021/ol901066x

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The transannular cyclization of germacrone with HSO3Cl at -78 degrees C by means of a concerted and regioselective mechanism gives rise to a bicyclo[6.2.0]decan-2-ylium intermediate ion, which evolves to unusual skeletons through subsequent cyclization and Wagner-Meerwein rearrangements. This novel germacra-1(10),4-diene cyclization could suggest the existence of a new biosynthetic pathway to sesquiterpenes.

引用

页码：4782 / 4785

页数：4

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