Catalytic enantioselective total synthesis of (-)-ar-Tenuifolene

被引：5

作者：

Shaw, Kundan ^{[1
]}

Niyogi, Sovan ^{[1
]}

Bisai, Vishnumaya ^{[1
,2
,3
]}

机构：

[1] Indian Inst Sci Educ & Res Bhopal, Dept Chem, Bhopal 462066, Madhya Pradesh, India

[2] Indian Inst Sci Educ & Res Berhampur, Dept Chem, Berhampur 760010, Odisha, India

[3] Indian Inst Sci Educ & Res Tirupati, Dept Chem, Tirupati 517507, Andhra Pradesh, India

来源：

TETRAHEDRON LETTERS | 2020年 / 61卷 / 20期

关键词：

Pd(II)-catalysis; Boronic acid addition; Sesquiterpenoids; ar-Teunifolene; CONJUGATE ADDITION; LAURANE SESQUITERPENE; ARYLBORONIC ACIDS; DERIVATIVES;

D O I：

10.1016/j.tetlet.2020.151850

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

First catalytic asymmetric total synthesis of aromatic sesquiterpene, (-)-ar-teunifolene (1) is featured (3 steps, 75% overall yields) from commercially available 3-methyl cyclohex-2-enone 16. The enantioenriched 3,3-disubstituted cyclohexanone 11 is obtained from Pd(II)-catalyzed enantioselective (p-tolyl) boronic acid addition to 3-methyl cyclohex-2-enone 16 in 90% ee, which is found to be the key intermediate. A diastereoselective methyllithium addition of this enantioenriched product followed by dehydration completes straightforward access to (-)-ar-teunifolene (1). (C) 2020 Elsevier Ltd. All rights reserved.

引用

页数：5

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