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A Formal Synthesis of (+)‐Cassiol Exploiting Meyers' Bicyclic Lactam Methodology
Author(s) -
Shen Xin,
Wu YiKang,
Zhang Fan
Publication year - 2002
Publication title -
chinese journal of chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.28
H-Index - 41
eISSN - 1614-7065
pISSN - 1001-604X
DOI - 10.1002/cjoc.20020201148
Subject(s) - chemistry , lactam , bicyclic molecule , alkylation , methyl iodide , iodide , chloride , stereochemistry , medicinal chemistry , organic chemistry , catalysis
A formal synthesis of (+)‐cassiol using (lS,2S)‐2‐amino‐1‐(4‐nitrophenyl)‐l,3‐propanediol as chiral auxiliary is reported. The quaternary chiral center in the molecule was constructed by sequential alkylation of a bicyclic lactam (prepared from the aforementioned auxiliary and 5‐oxo‐heptanoic acid) with methyl iodide and benzyloxymethyl chloride.