Role of the Nozaki-Hiyama-Takai-Kishi Reaction in the Synthesis of Natural Products

被引：140

作者：

Gil, Alejandro ^{[1
,2
]}

Albericio, Fernando ^{[1
,2
,3
,5
]}

Alvarez, Mercedes ^{[1
,2
,4
]}

机构：

[1] ChemBio Lab, Barcelona Sci Pk,Baldiri Reixac 10, E-08028 Barcelona, Spain

[2] Networking Ctr Bioengn Biomat & Nanomed, CIBER BBN, Barcelona Sci Pk,Baldiri Reixac 10, Barcelona 08028, Spain

[3] Univ Barcelona, Dept Organ Chem, Sch Chem, E-08028 Barcelona, Spain

[4] Univ Barcelona, Fac Pharm, Lab Organ Chem, E-08028 Barcelona, Spain

[5] Univ KwaZulu Natal, ZA-4001 Durban, South Africa

来源：

CHEMICAL REVIEWS | 2017年 / 117卷 / 12期

关键词：

ENANTIOSELECTIVE TOTAL-SYNTHESIS; 1ST TOTAL-SYNTHESIS; NI(II)/CR(II)-MEDIATED COUPLING REACTION; STEREOSELECTIVE TOTAL-SYNTHESIS; CYTOTOXIC MACROLIDE GLYCOSIDES; 2ND-GENERATION TOTAL-SYNTHESIS; PROTEIN PHOSPHATASE 2A; FORMAL TOTAL-SYNTHESIS; ASYMMETRIC-SYNTHESIS; MARINE TOXIN;

D O I：

10.1021/acs.chemrev.7b00144

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The Nozaki-Hiyama-Takai-Kishi (NHTK) reaction was discovered in the late 1970s and, since then, its main application has been its use in total synthesis. In this comprehensive review, the efficiency of the NHKT reaction in the synthesis of a great number of different scaffolds present in complex natural products is analyzed. The preparation of enol and allylic and propargylic alcohol motifs is discussed, highlighting factors such as yield, chemoselectivity, stereoselectivity, or the importance of protecting groups. The review is divided into two main sections: intermolecular and intramolecular NHTK reactions. A final discussion about the current "state-of-art" and future perspectives for the use of this transformation in total synthesis is also included.

引用

页码：8420 / 8446

页数：27

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