Formal Synthesis of Gracilamine Using Rh(I)-Catalyzed [3+2+1] Cycloaddition of 1-Yne-Vinylcyclopropanes and CO

被引：40

作者：

Bose, Sritama ^{[1
]}

Yang, Jun ^{[1
]}

Yu, Zhi-Xiang ^{[1
]}

机构：

[1] Peking Univ, Coll Chem, Key Lab Bioorgan Chem & Mol Engn, BNLMS,Minist Educ, Beijing 100871, Peoples R China

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2016年 / 81卷 / 15期

关键词：

AROMATIC-ALDEHYDES; AMARYLLIDACEAE ALKALOIDS; SCELETIUM ALKALOIDS; STEREOCENTERS; ALKYNYLATION; ADDITIONS;

D O I：

10.1021/acs.joc.6b00608

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Reported here is a formal synthesis of gracilamine using Rh(I)-catalyzed [3 + 2 + 1] reaction of yne-VCP (+/-)-4 and CO. The key reaction gave the cycloadduct (+/-)-trans-3 with the A-B-C core structure of gracilamine. This advanced intermediate was further transformed to Gao's intermediate (+/-)-2 via regular transformations to realize the formal synthesis of gracilamine. The present strategy was used to accomplish the asymmetric formal synthesis of gracilamine using chiral substrate (+)-4.

引用

页码：6757 / 6765

页数：9

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