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

被引：41
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.
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收藏
页码：6757 / 6765
页数：9
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