Studies Toward the Total Synthesis of Schinortriterpenoids: Diastereoselective Synthesis of the Left‐Hand Fragment | Zendy

Yagita Ryotaro | Zendy; Irie Kazuhiro | Zendy; Tsukano Chihiro | Zendy

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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.

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