A New Access to the 6,8-Dioxabicyclo[3.2.1]octane Ring System Using a Three-Component Reaction: Enantioselective Synthesis of (+)-iso-exo-Brevicomin

被引：17

作者：

Bouziane, Asmae ^{[1
]}

Regnier, Thomas ^{[1
]}

Carreaux, Francois ^{[1
]}

Carboni, Bertrand ^{[1
]}

Bruneau, Christian ^{[1
]}

Renaud, Jean-Luc ^{[2
]}

机构：

[1] Univ Rennes 1, CNRS, UMR 6226, F-35042 Rennes, France

[2] CNRS, UMR 6507, Lab Chim Mol & Thioorgan, F-14050 Caen, France

来源：

SYNLETT | 2010年 / 02期

关键词：

natural product; asymmetric catalysis; cycloaddition; boron; redox isomerization; DIELS-ALDER/ALLYLBORATION SEQUENCE; FUSED BICYCLIC ACETALS; MOUNTAIN PINE-BEETLE; ASYMMETRIC-SYNTHESIS; ALLYLIC ALCOHOLS; PROPARGYLIC ALCOHOLS; REDOX ISOMERIZATION; CLOSING METATHESIS; CARBONYL-COMPOUNDS; CYCLOISOMERIZATION;

D O I：

10.1055/s-0029-1218561

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The combination of a catalytic hetero-Diels-Alder-allylboration sequence and a ruthenium-catalyzed isomerization of an allylic alcohol moiety as key steps open a new route for the asymmetric synthesis of 6,8-dioxabicyclo[3.2.1]octane subunits. The application of this strategy to the synthesis of (+)-iso-exo-brevicomin is also reported.

引用

页码：207 / 210

页数：4

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