Formal total synthesis of N-methylmaysenine.
A novel synthetic approach for the formal total synthesis of N-methylmaysenine (1) has been developed. Key steps involve the Ti-mediated vinylogous Mukaiyama aldol reaction of chiral ketene silyl N,O-acetal with beta-dithiane-substituted aldehyde, an aldol condensation, and a ring-closing metathesis reaction.
Wang
Lin
L
Key Laboratory of Bioorganic Chemistry and Molecular Engineering of Ministry of Education, College of Chemistry, and Laboratory of Chemical Genomics, Shenzhen Graduate School, Peking University, Beijing 100871, China.
Gong
Jianxian
J
Deng
Lujiang
L
Xiang
Zheng
Z
Chen
Zhixing
Z
Wang
Yuefan
Y
Chen
Jiahua
J
Yang
Zhen
Z
D000447:Aldehydes / Q000737:chemistry*; D002384:Catalysis; D003500:Cyclization; D008453:Maytansine / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry; D015394:Molecular Structure
D000447:Aldehydes; C540239:N-methylmaysenine; D008453:Maytansine; C116609:3-hydroxybutanal