Premium
Concise Stereoselective Synthesis of Oxaspirocycles with 1‐Tosyl‐1,2,3‐triazoles: Application to the Total Syntheses of (±)‐Tuberostemospiroline and (±)‐Stemona‐lactam R
Author(s) -
Fu Junkai,
Shen Hongjuan,
Chang Yuanyuan,
Li Chuangchuang,
Gong Jianxian,
Yang Zhen
Publication year - 2014
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201403756
Subject(s) - tosyl , lactam , stereoselectivity , chemistry , stereochemistry , organic chemistry , catalysis
A 4‐substituted‐1‐tosyl‐1,2,3‐triazole‐based stereoselective synthesis of structurally diverse oxaspirocycles is reported. The synthesis involves Rh‐catalyzed loss of nitrogen from 4‐substituted‐1‐tosyl‐1,2,3‐triazoles, Grignard reaction, and a ring‐closing metathesis reaction as key steps. By employing readily available and stable 4‐substituted‐1‐tosyl‐1,2,3‐triazoles as surrogates of diazo compounds and nitrogen sources, two types of oxaspirocycles were obtained. The latter compounds, which contain adjacent nitrogen stereocenters, could serve as the core structures of many natural products. This chemistry has been successfully applied to the total syntheses of (±)‐tuberostemospiroline and (±)‐stemona‐lactam R.