Chemo- and stereoselective six-membered oxonium ylide formation-[2,3]-sigmatropic rearrangement of 2-diazo-3-ketoesters with dirhodium(II) catalyst and its application to the synthesis of (+)-tanikolide

被引：6
作者：
Jinnouchi, Hikari [1 ]
Nambu, Hisanori [1 ]
Takahashi, Kanae [1 ]
Fujiwara, Tomoya [1 ]
Yakura, Takayuki [1 ]
机构：
[1] Univ Toyama, Grad Sch Med & Pharmaceut Sci, Sugitani, Toyama 9300194, Japan
来源：
TETRAHEDRON | 2019年 / 75卷 / 16期
基金：
日本学术振兴会;
关键词：
Oxonium ylide; Rearrangement; Rhodium; Chemoselectivity; Stereoselectivity; INTRAMOLECULAR GENERATION; SIGMATROPIC REARRANGEMENT; OXIDATIVE CLEAVAGE; AMPHIDINOLIDES C; TETRAHYDROFURAN-2-METHANOLS; CONSTRUCTION; FRAGMENT; CORE;
D O I：
10.1016/j.tet.2019.03.012
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Dirhodium(II)-catalyzed oxonium ylide formation-[2,3]-sigmatropic rearrangement of 6-allyloxy-2-diazo-3-ketoesters possessing a C-6 substituent is described. The reaction of 6-alkyl- or 6-aryl-substituted 6-allyloxy-2-diazo-3-ketoesters with a catalytic amount of Rh-2(S-PTTL)(4) proceeded in a chemoselective and stereoselective manner to provide 6-substituted 2-allyl-3-oxotetrahydropyran-2-carboxylates in good yields and with high diastereoselectivities. To demonstrate the utility of this sequential reaction, we conducted the total synthesis of (+)-tanikolide, in which the construction of the delta-lactone skeleton was achieved by employing a 2-iodobenzamide-catalyzed oxidative cleavage of tetrahydropyran-2-methanol. (C) 2019 Elsevier Ltd. All rights reserved.
引用
收藏
页码：2436 / 2445
页数：10
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