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Studies Toward the Total Synthesis of Schinortriterpenoids: Diastereoselective Synthesis of the Left‐Hand Fragment
Author(s) -
Yagita Ryotaro,
Irie Kazuhiro,
Tsukano Chihiro
Publication year - 2021
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.202100510
Subject(s) - chemistry , terpene , stereoselectivity , fragment (logic) , stereochemistry , tricyclic , cycloaddition , total synthesis , oxygen atom , organic chemistry , molecule , catalysis , computer science , programming language
Schinortriterpenoids, such as pre‐schisanartanin A and arisanlactone C, are complex and highly oxygenated polycyclic terpenes. In this study, the left‐hand fragment of this class terpenes, which possesses oxygen‐functionality at C19, was synthesized through [3+2] cycloaddition with excellent diastereoselectivity. This stereoselectivity was investigated by computational studies. Further selective transformation provided a tricyclic skeleton with the desired stereochemistry.