Directed Orthometalation and the Asymmetric Total Synthesis of N-Deoxymilitarinone A and Torrubiellone B

被引：23

作者：

Ding, Feiqing ^{[1
]}

William, Ronny ^{[1
]}

Leow, Min Li ^{[1
]}

Chai, Hua ^{[1
]}

Fong, Jacqueline Zi Mei ^{[1
]}

Liu, Xue-Wei ^{[1
]}

机构：

[1] Nanyang Technol Univ, Sch Phys & Math Sci, Div Chem & Biol Chem, Singapore 637371, Singapore

来源：

ORGANIC LETTERS | 2014年 / 16卷 / 01期

关键词：

STEREOSELECTIVE TOTAL-SYNTHESIS; ABSOLUTE-CONFIGURATION; PAECILOMYCES-MILITARIS; PYRIDONE ALKALOIDS; BEAUVERIA-BASSIANA; SIDE-CHAIN; METABOLITES; TENELLIN; PYRIDOVERICIN; CONVERGENT;

D O I：

10.1021/ol402820d

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A diverted total synthesis (DTS) approach to the total synthesis of pyridone alkaloids N-deoxymilitarinone A (8) and torrubiellone B (10) has been developed. The common intermediate 14 was first assembled by a dual directed orthometalation process using a methoxymethyl group as directed metalation group. Other crucial steps include the assembly of polyenes under aldol condensation for DTS using general and concise strategy and diastereoselective synthesis of the syn-dimethyl array by an Evans aldol reaction.

引用

页码：26 / 29

页数：4

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