Palladium-Catalyzed α-Arylation of Cyclic Vinylogous Esters for the Synthesis of γ-Arylcyclohexenones and Total Synthesis of Aromatic Podocarpane Diterpenoids

被引：20
|
作者：
Hou, Wen-Yi [1 ]
Wu, Yen-Ku [1 ]
机构：
[1] Natl Chiao Tung Univ, Dept Appl Chem, 1001 Univ Rd, Hsinchu 30010, Taiwan
来源：
ORGANIC LETTERS | 2017年 / 19卷 / 05期
关键词：
C-H BONDS; QUATERNARY CENTERS; ARYL HALIDES; ALL-CARBON; ALKYLATION; KETONES; CYCLOHEXENONES; STEREOCENTERS; EQUIVALENTS; REDUCTION;
D O I：
10.1021/acs.orglett.7b00268
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Described is a method for the formal gamma-arylation of cyclohexenones allowing synthesis of a remote all-carbon quaternary center. The process involves the palladium-catalyzed alpha-arylation of a alpha-substituted cyclic vinylogous ester followed by the Stork-Danheiser transposition. The synthetic utility of this protocol is featured in the total syntheses of (+/-)-12-hydroxy-13-methylpodocarpa-8,11,13-trien-3-one, (+/-)-3 beta,12-dihydroxy-13-methylpodocarpane-8,11,13-triene, and (+/-)-O-methyl nimbinone.
引用
收藏
页码：1220 / 1223
页数：4
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