Highly enantioselective construction of a quaternary carbon centre by the Pummerer-type reaction: a total synthesis of (–)-sibirine

1991 ◽  
pp. 1409-1411 ◽  
Author(s):  
Takeshi Imanishi ◽  
Toshiki Kurumada ◽  
Naoyoshi Maezaki ◽  
Kenji Sugiyama ◽  
Chuzo Iwata
Keyword(s):  
Total Synthesis ◽  
Quaternary Carbon ◽  
Type Reaction

ChemInform Abstract: Highly Enantioselective Construction of a Quaternary Carbon Centre by the Pummerer Type Reaction: A Total Synthesis of (-)-Sibirine.

ChemInform ◽  
2010 ◽  
Vol 23 (14) ◽  
pp. no-no
Author(s):  
T. IMANISHI ◽  
T. KURUMADA ◽  
N. MAEZAKI ◽  
K. SUGIYAMA ◽  
C. IWATA
Keyword(s):  
Total Synthesis ◽  
Quaternary Carbon ◽  
Type Reaction

scholarly journals Recent development and applications of semipinacol rearrangement reactions

2021 ◽  
Author(s):  
Xiao-Ming Zhang ◽  
Bao-Sheng Li ◽  
Shao-Hua Wang ◽  
Kun Zhang ◽  
Fu-Min Zhang ◽  
...  
Keyword(s):  
Total Synthesis ◽  
Quaternary Carbon ◽  
Carbon Formation ◽  
Semipinacol Rearrangement ◽  
Rearrangement Reactions

The recent development of semipinacol rearrangement is reviewed, highlighting its application in β-functionalized ketone synthesis, quaternary carbon formation and total synthesis.

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.

Construction of an asymmetric quaternary carbon via an asymmetric aza-Claisen rearrangement and its application in the total synthesis of (+)-α-cuparenone

2012 ◽  
Vol 23 (10) ◽  
pp. 739-741 ◽  
Author(s):  
Takeshi Nishii ◽  
Fumiaki Miyamae ◽  
Makoto Yoshizuka ◽  
Hiroto Kaku ◽  
Mitsuyo Horikawa ◽  
...  
Keyword(s):  
Total Synthesis ◽  
Claisen Rearrangement ◽  
Quaternary Carbon

Total Synthesis of Bouchardatine

2013 ◽  
Vol 66 (9) ◽  
pp. 1112 ◽  
Author(s):  
Nilesh H. Naik ◽  
Tukaram D. Urmode ◽  
Arun K. Sikder ◽  
Radhika S. Kusurkar
Keyword(s):  
Total Synthesis ◽  
Intramolecular Cyclization ◽  
Type Reaction ◽  
Naturally Occurring

Two new, efficient and simple routes using Heck-type reaction and intramolecular cyclization were developed for the synthesis of the naturally occurring cytotoxic alkaloid 2-(4-oxo-3,4-dihydroquinazolin-2-yl)-1H-indole-3-carbaldehyde (bouchardatine).

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