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Efficient Enantioselective Total Synthesis of (−)‐Horsfiline
Author(s) -
Hong Suckchang,
Jung Myunggi,
Park Yohan,
Ha Min Woo,
Park Cheonhyoung,
Lee Myungmo,
Park Hyeunggeun
Publication year - 2013
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.201301008
Subject(s) - enantioselective synthesis , total synthesis , computer science , chemistry , stereochemistry , organic chemistry , catalysis
A new efficient and concise enantioselective synthetic method for (−)‐horsfiline is reported. (−)‐Horsfiline could be obtained from diphenylmethyl tert ‐butyl malonate in 9 steps (32 %,>99 % ee ) by using the enantioselective phase‐transfer catalytic allylation (91 % ee ) as the key step. This approach can be applied as a practical route for the large‐scale synthesis of spirooxindole natural products, which enables a systematic investigation of their biological activity to be performed.