Regiocontrol in Pd(0)‐Mediated Couplings of a Bis(enol triflate) with Alkynes — Stereoselective Syntheses of Monocyclic Dienediynes Related to the Neocarzinostatin Chromophore
- 1 January 1992
- journal article
- research article
- Published by Wiley in European Journal of Inorganic Chemistry
- Vol. 125 (1) , 271-278
- https://doi.org/10.1002/cber.19921250143
Abstract
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.Keywords
This publication has 24 references indexed in Scilit:
- Chemie und Biologie von Endiin‐Cytostatica/AntibioticaAngewandte Chemie, 1991
- Synthesis and Cycloaromatization of a Neocarzinostatin Chromophore Analogue Equipped with an Intramolecular NucleophileSynlett, 1991
- Synthesis of the neocarzinostatin chromophore A core diynene structure using an η2-hexacarbonyidicobalt mediated Aldol reactionJournal of the Chemical Society, Chemical Communications, 1991
- General methodology for the synthesis of neocarzinostatin chromophore analogs: intramolecular chromium-mediated closures for strained ring synthesisJournal of the American Chemical Society, 1990
- The 10-membered ring analogs of neocarzinostatin chromophore: design, synthesis and mode of decompositionJournal of the American Chemical Society, 1989
- Stereochemical assignment of neocarzinostatin chromophore. Structures of neocarzinostatin chromophore-methyl thioglycolate adductsJournal of the American Chemical Society, 1988
- Palladium-Catalyzed Reaction of Enol Triflates with 1-Alkynes. A New Route to Conjugated EnynesSynthesis, 1986
- An empirical method for correcting diffractometer data for absorption effectsActa Crystallographica Section A Foundations of Crystallography, 1983
- Improved Syntheses of 2-Hydroxymethylenecyclopentanone (2-Formylcyclopentanone) and Spiro[4.5]dec-6-en-1,8-dioneSynthesis, 1983
- Rapid chromatographic technique for preparative separations with moderate resolutionThe Journal of Organic Chemistry, 1978