Premium
Regiocontrol in Pd(0)‐Mediated Couplings of a Bis(enol triflate) with Alkynes — Stereoselective Syntheses of Monocyclic Dienediynes Related to the Neocarzinostatin Chromophore
Author(s) -
Scheuplein Stefan W.,
Harms Klaus,
Brückner Reinhard,
Suffert Jean
Publication year - 1992
Publication title -
chemische berichte
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.667
H-Index - 136
eISSN - 1099-0682
pISSN - 0009-2940
DOI - 10.1002/cber.19921250143
Subject(s) - trifluoromethanesulfonate , chemistry , stereoselectivity , enol , stereochemistry , chromophore , enol ether , organic chemistry , catalysis
The stereoselective synthesis of (Z)‐dienediynes 2 related to the neocarzinostatin chromophore 1 is described. (Z)‐Bis(enol triflate) 3 , accessible stereoselectively from 2‐formylcyclopentanone in 2 steps, serves as the key intermediate. It is subjected to consecutive Pd(0)‐catalyzed couplings with two different alkynes and furnishes 2 via monocoupling products 8 .