Practical Asymmetric Synthesis of Amathaspiramides B, D, and F

被引：22

作者：

Cai, Sen-Lin ^{[1
]}

Song, Ran ^{[1
]}

Dong, Han-Qing ^{[2
]}

Lin, Guo-Qiang ^{[1
,2
]}

Sun, Xing-Wen ^{[1
]}

机构：

[1] Fudan Univ, Dept Chem, 220 Handan Rd, Shanghai 200433, Peoples R China

[2] Chinese Acad Sci, Shanghai Inst Organ Chem, 345 Lingling Rd, Shanghai 200032, Peoples R China

来源：

ORGANIC LETTERS | 2016年 / 18卷 / 09期

基金：

中国国家自然科学基金;

关键词：

TERT-BUTANESULFINYL IMINES; N-ALKYL IMINES; MEDIATED ALLYLATION; VINYL CARBODIIMIDES; AMATHIA-WILSONI; AMINES; ALKALOIDS; REDUCTION; ACCESS;

D O I：

10.1021/acs.orglett.6b00588

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The practical asymmetric synthesis of amathaspiramides B, D, and F has been accomplished by utilizing an aza-Barbier allylation as the key step to construct the common intermediate with two adjacent stereocenters. A kinetically controlled cyclization to build the challenging thermodynamically less stable 8R-hemiaminal moiety is also important in the synthesis of amathaspiramide D. The route is readily scalable, and gram quantity of the final product D has been prepared.

引用

页码：1996 / 1999

页数：4

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