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Total Synthesis of Gelsedilam by Means of a Thiol‐Mediated Diastereoselective Conjugate Addition–Aldol Reaction
Author(s) -
Huang YouMing,
Liu Yang,
Zheng ChangWu,
Jin QiaoWen,
Pan Lu,
Pan RenMing,
Liu Jun,
Zhao Gang
Publication year - 2016
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.201604620
Subject(s) - aldol reaction , conjugate , intramolecular force , total synthesis , thiol , ring (chemistry) , chemistry , stereochemistry , michael reaction , enantioselective synthesis , addition reaction , combinatorial chemistry , organic chemistry , catalysis , mathematics , mathematical analysis
The total synthesis of gelsedilam, which features a highly diastereoselective thiol conjugate addition–intramolecular aldol reaction to install the strained and caged [3.2.2] bridged ring system and highly efficient NiCl 2 /NaBH 4 ‐mediated four‐step transformation in one‐pot to construct its five‐membered lactam ring is reported. The synthesis requires only 18 linear steps from the known compounds, providing useful strategies for the construction of the intricate ring system in the synthesis of related gelsedine‐type alkaloids.