Enantioselective Total Synthesis of Pentacyclic Proaporphine Alkaloid (−)‐Misramine | Zendy

Pu LiuYang | Zendy; Yang Fan | Zendy; Chen JiQiang | Zendy; Xiong Ying | Zendy; Xie JianHua | Zendy; Zhou QiLin | Zendy

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Enantioselective Total Synthesis of Pentacyclic Proaporphine Alkaloid (−)‐Misramine

Author(s) -

Pu LiuYang,

Yang Fan,

Chen JiQiang,

Xiong Ying,

Xie JianHua,

Zhou QiLin

Publication year - 2021

Publication title -

advanced synthesis and catalysis

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 1.541

H-Index - 155

eISSN - 1615-4169

pISSN - 1615-4150

DOI - 10.1002/adsc.202001139

Subject(s) - enantioselective synthesis , chemistry , pinacol , moiety , alkaloid , stereochemistry , total synthesis , absolute configuration , organic chemistry , catalysis

An enantioselective total synthesis of pentacyclic proaporphine alkaloid (−)‐misramine has been achieved. The synthetic route features a Pictet‐Spengler cyclization to construct the fused B and C rings and a sequence of Baeyer‐Villiger oxidation, Pinnick oxidation, and pinacol‐type cyclization to install the α‐hydroxy ketal moiety. The absolute configuration of the pentacyclic framework was elucidated by X‐ray single‐crystal analyses of (−)‐11‐demethoxymisramine.

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