Synthesis of 2,6-trans-Tetrahydropyrans Using a Palladium-Catalyzed Oxidative Heck Redox-Relay Strategy

被引：5

作者：

Bonfield, Holly E. ^{[1
,2
,3
]}

Edge, Colin M. ^{[2
]}

Reid, Marc ^{[1
]}

Kennedy, Alan R. ^{[1
]}

Pascoe, David D. ^{[2
]}

Lindsay, David M. ^{[1
]}

Valette, Damien ^{[2
,4
]}

机构：

[1] Univ Strathclyde, Dept Pure & Appl Chem, Glasgow G1 1XL, Scotland

[2] GSK, Drug Subst Dev, Gunnels Wood Rd, Stevenage SG1 2NY, England

[3] Apex Mol Ltd, Alderley Pk, Alderley Edge SK10 4TG, England

[4] MSD R&D Innovat Ctr, 120 Moorgate, London EC2M 6UR, England

来源：

ORGANIC LETTERS | 2024年 / 26卷 / 14期

基金：

英国工程与自然科学研究理事会;

关键词：

ASYMMETRIC-SYNTHESIS; TETRAHYDROPYRAN; CYCLIZATIONS; HETEROCYCLES; ARYLATIONS;

D O I：

10.1021/acs.orglett.3c03866

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The C-aryl-tetrahydropyran motif is prevalent in nature in a number of natural products with biological activity; however, this challenging architecture still requires novel synthetic approaches. We demonstrate the application of a stereoselective Heck redox-relay strategy for the synthesis of functionalized 2,6-trans-tetrahydropyrans in excellent selectivity in a single step from an enantiopure dihydropyranyl alcohol, proceeding through a novel exo-cyclic migration. The strategy has also been applied to the total synthesis of a trans-epimer of the natural product centrolobine in excellent yield and stereoselectivity.

引用

页码：2857 / 2861

页数：5

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