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Gold(I)‐Catalyzed Furan‐yne Cyclizations Involving 1,2‐Rearrangement: Efficient Synthesis of Functionalized 1‐Naphthols and Its Application to the Synthesis of Wailupemycin G
Author(s) -
Chen Yifeng,
Wang Lu,
Sun Ning,
Xie Xin,
Zhou Xiaobo,
Chen Haoyi,
Li Yuxue,
Liu Yuanhong
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.201403113
Subject(s) - furan , stereoselectivity , propargyl , moiety , chemistry , enone , catalysis , combinatorial chemistry , stereochemistry , organic chemistry
Gold‐catalyzed cascade cyclization/1,2‐rearrangement of 1‐(2‐furanyl)phenyl propargyl alcohols has been developed, which provides a rapid and efficient access to multisubstituted 1‐naphthols bearing an enal or enone moiety with high stereoselectivity. The ( Z )‐ or ( E )‐stereochemistry can be easily controlled by choosing protected‐ or non‐protected substrates. The utility of the methodology has been illustrated in the first total synthesis of wailupemycin G.