Catalytic Asymmetric Synthesis and Stereochemical Revision of (+)-Cryptoconcatone H

被引：22

作者：

-Felice, Franco Della ^{[1
]}

Sarotti, Ariel M. ^{[2
]}

Pilli, Ronaldo A. ^{[1
]}

机构：

[1] Univ Estadual Campinas, Inst Chem, BR-13084971 Campinas, SP, Brazil

[2] Univ Nacl Rosario, CONICET, Fac Ciencias Bioquim & Farmaceut, Inst Quim Rosario, Suipacha 531,S2002LRK, Rosario, Santa Fe, Argentina

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2017年 / 82卷 / 17期

基金：

巴西圣保罗研究基金会;

关键词：

STEREOSELECTIVE-SYNTHESIS; ABSOLUTE-CONFIGURATION; CARBONYL ALLYLATION; 1,3-DIOL ACETONIDES; OXIDATION LEVEL; NMR; ASSIGNMENT; ALCOHOL; COMPLEX; ACETATE;

D O I：

10.1021/acs.joc.7b01378

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The total synthesis and structural revision of (+)-cryptoconcatone H are described. Guided by computational studies for the final structure assignment, the stereogenic centers at the tetrahydropyran moiety of (+)-cryptoconcatone H were assembled through catalytic asymmetric methodologies: Krische allylation, cross-metathesis reaction, and THP formation via Pd(II)-catalyzed cyclization. Finally, a Krische allylation reaction established the last stereocenter, and the lactone moiety was formed by ring-closing metathesis.

引用

页码：9191 / 9197

页数：7

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