D- and L-Erythrose as Sources of Chiral Quaternary Carbon Centers. Total Synthesis of (-)-Malyngolide and (+)-Tanikolide.

ChemInform ◽  
2003 ◽  
Vol 34 (26) ◽  
Author(s):  
Alexandros E. Koumbis ◽  
Kyriaki M. Dieti ◽  
Myrofora G. Vikentiou ◽  
John K. Gallos
Keyword(s):  
Total Synthesis ◽  
Quaternary Carbon ◽  
Carbon Centers

d- and l-Erythrose as sources of chiral quaternary carbon centers. Total synthesis of (−)-malyngolide and (+)-tanikolide

2003 ◽  
Vol 44 (12) ◽  
pp. 2513-2516 ◽  
Author(s):  
Alexandros E. Koumbis ◽  
Kyriaki M. Dieti ◽  
Myrofora G. Vikentiou ◽  
John K. Gallos
Keyword(s):  
Total Synthesis ◽  
Quaternary Carbon ◽  
Carbon Centers

Kinetic resolution of oxime esters with lipases — synthesis of enantiomerically enriched building blocks with quaternary carbon centers and formal total synthesis of perhydro histrionicotoxin

2002 ◽  
Vol 80 (6) ◽  
pp. 686-691 ◽  
Author(s):  
Nicole Diedrichs ◽  
Ralf Krelaus ◽  
Ina Gedrath ◽  
Bernhard Westermann
Keyword(s):  
Substrate Specificity ◽  
Total Synthesis ◽  
Solvent Effects ◽  
Kinetic Resolution ◽  
Building Blocks ◽  
Beckmann Rearrangement ◽  
Optically Active ◽  
Quaternary Carbon ◽  
Carbon Centers

Enantiomerically enriched oximes bearing stereogenic quaternary carbon centers can be obtained by lipase-catalyzed kinetic resolution of oxime esters. Substrate specificity, solvent effects, and the use of different lipases are discussed. Kinetic resolution of butyrylated oximes by lipase PS in the presence of n-butanol gave the best ee-values of both the saponified oxime and the residual oxime ester. Subsequent stereospecific Beckmann rearrangement of an enantiomerically enriched oxime provided lactams, which could be employed for the synthesis of optically active perhydro histrionicotoxin.Key words: oxime, lipase, kinetic resolution, Beckmann rearrangement, perhydro histrionicotoxin.

scholarly journals Synthesis of Cyclohexane-Angularly-Fused Triquinanes

Synthesis ◽  
2020 ◽  
Author(s):  
Hongjun Jeon ◽  
Jeffrey D. Winkler
Keyword(s):  
Total Synthesis ◽  
Synthetic Approach ◽  
Quaternary Carbon ◽  
Carbon Centers ◽  
Naturally Occurring

AbstractCyclohexane-angularly-fused triquinanes, 6-5-5-5 tetra­cycles, have attracted the attention of synthetic chemists due to their highly congested core structures and multiple quaternary carbon centers. This review focuses on the six completed total synthesis of naturally occurring cyclohexane-angularly-fused triquinanes in addition to seven notable methodologies that have been developed for the synthesis of these structures.1 Introduction2 6-5-5-5 Tetracycles Containing a Linear Triquinane2.1 Total Synthesis of Cyclopiane Diterpenes2.2 Synthetic Approach toward Aberrarane Diterpenes2.3 Intermediates in the Total Synthesis of Magellanine-Type Alkaloids3 6-5-5-5 Tetracycles Containing an Angular Triquinane3.1 Total Synthesis of Waihoensene3.2 Miscellaneous Approaches4 Conclusion

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