Total Synthesis and Determination of the Absolute Configuration of Berkeleylactone I

被引：1

作者：

Mandal, Sudip ^{[1
]}

Mahananda, Dora ^{[1
]}

Paladugu, Dileep ^{[1
]}

Thirupathi, Barla ^{[1
]}

机构：

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

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2024年 / 89卷 / 06期

关键词：

DRUG DISCOVERY; MACROCYCLES; ALCOHOLS;

D O I：

10.1021/acs.joc.4c00178

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Herein, we report the first total synthesis of berkeleylactone I and its 12S diastereomer. Consequently, this chemical synthesis allowed us to establish the unknown absolute stereochemistry at the C-12 center as 12R, which was unidentified by the isolation group. This synthetic approach includes several critical reactions, such as the Sharpless asymmetric dihydroxylation, Baran's Ni-catalyzed alkyl-alkyl cross-coupling reaction, Brown allylation, Mitsunobu reaction, and ring-closing metathesis, as key steps.

引用

页码：4165 / 4175

页数：11

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