Premium
The Effect of Acetylene Substituents on a Pd II ‐Catalyzed Cycloisomerization. Total Synthesis of (–)‐Sterepolide and Assignment of Absolute Stereochemistry
Author(s) -
Trost Barry M.,
Hipskind Philip A.,
Chung John Y. L.,
Chan Chuen
Publication year - 1989
Publication title -
angewandte chemie international edition in english
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 0570-0833
DOI - 10.1002/anie.198915021
Subject(s) - cycloisomerization , cyclopentane , catalysis , chemistry , alkyne , acetylene , ligand (biochemistry) , stereochemistry , palladium , medicinal chemistry , ethylenediamine , absolute configuration , total synthesis , organic chemistry , receptor , biochemistry
Cyclopentane units in natural products such as (–)‐stereopolide 3 are not easy to synthesize. A novel route starts from the non‐terminal alkyne 1 . Its cycloisomerization to 2 is possible in the presence of palladium( II ) acetate and the ligand N,N ′‐bis(benzylidene)ethylenediamine. This catalytic system also cyclizes other enynes of the type 1 with e.g. CH 2 OCH 3 or CH 3 instead of OSiMe 2 t Bu—where Pd(OAc) 2 alone fails (R = p ‐H 3 COC 6 H 4 CH 2 ).