Ti(III)-promoted cyclizations.: Application to the synthesis of (E)-endo-bergamoten-12-oic acids.: Moth oviposition stimulants isolated from Lycopersicon hirsutum

被引：35

作者：

Bermejo, Francisco A. ^{[1
]}

Fernandez Mateos, Alfonso ^{[1
]}

Marcos Escribano, Andres ^{[1
]}

Martin Lago, Rodrigo ^{[1
]}

Mateos Buron, Lydia ^{[1
]}

Rodriguez Lopez, Maria ^{[1
]}

Rubio Gonzalez, Rosa ^{[1
]}

机构：

[1] Univ Salamanca, Fac Quim, Dept Quim Organ, E-37008 Salamanca, Spain

来源：

TETRAHEDRON | 2006年 / 62卷 / 38期

关键词：

sesquiterpenoids; beta-halomethacrylates; (E)-beta-endo-bergamoten-12-oic acids; (S)-(+)-carvone;

D O I：

10.1016/j.tet.2006.07.020

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The Ti (111)-promoted radical cyclization of epoxyenone 8 is described as the key step to access the diol 10 as a convenient starting material of the target molecules. The synthesis of beta-(E)-endo-bergamoten-12-oic acid 2a from (+)-8,9-epoxycarvone 8 was successfully achieved by Suzuki-Miyaura coupling of the terminal alkene 20 with beta-iodomethacrylate 21c, followed by deprotection and dehydration processes. Moreover, synthesis of the alpha-(E)-endo-1-hydroxy-bergamoten-12-oic acid derivative 34 was achieved by iterative elongation processes of the diol 10 lateral chain. (c) 2006 Elsevier Ltd. All rights reserved.

引用

页码：8933 / 8942

页数：10

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