Regiocontrol in Pd(0)‐Mediated Couplings of a Bis(enol triflate) with Alkynes — Stereoselective Syntheses of Monocyclic Dienediynes Related to the Neocarzinostatin Chromophore | Zendy

Scheuplein Stefan W. | Zendy; Harms Klaus | Zendy; Brückner Reinhard | Zendy; Suffert Jean | Zendy

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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 .

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