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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.