ChemInform Abstract: Menthol Mediated Optical Resolution of 10-Oxatricyclodecadienones. Application in the Enantioselective Synthesis of Cyclopentenoids.

ChemInform ◽  
1990 ◽  
Vol 21 (42) ◽  
Author(s):  
A. A. M. HOUWEN-CLAASSEN ◽  
A. J. H. KLUNDER ◽  
B. ZWANENBURG ◽  
P. T. BEURSKENS ◽  
F. G. MOERS ◽  
...  
Keyword(s):  
Optical Resolution ◽  
Enantioselective Synthesis

Menthol mediated optical resolution of 10-oxatricyclodecadienones. Application in the enantioselective synthesis of cyclopentenoids

Tetrahedron ◽  
1990 ◽  
Vol 46 (12) ◽  
pp. 4283-4294 ◽  
Author(s):  
Adrie A.M. Houwen-Claassen ◽  
A.J.H. Klunder ◽  
B. Zwanenburg ◽  
Paul T. Beurskens ◽  
F.G. Moers ◽  
...  
Keyword(s):  
Optical Resolution ◽  
Enantioselective Synthesis

Synthesis of naturally occurring o-heterocyclic compounds of biological activity

2004 ◽  
Vol 76 (5) ◽  
pp. 1025-1032 ◽  
Author(s):  
Sándor Antus ◽  
Katalin Gulácsi ◽  
László Juhász ◽  
Loránd Kiss ◽  
Tibor Kurtán
Keyword(s):  
Biological Activity ◽  
Circular Dichroism ◽  
Total Synthesis ◽  
Heterocyclic Compounds ◽  
Optical Resolution ◽  
Enantioselective Synthesis ◽  
Ring Closure ◽  
X Ray ◽  
Naturally Occurring ◽  
Circular Dichroïsm

The total synthesis of (−)-cabenegrin A-I was achieved via (−)-6aR,11aR maackiain, which was obtained by optical resolution of racemic maackiain using S-(−)-alpha-methylbenzyl isocyanate. The synthesis of rac-maackiain was performed both with the Heck oxyarylation of 7-benzyloxy-2H-chromene and the BF3OEt2 mediated ring closure of isoflavan-4-ol derivatives, the latter of which provided much higher yields. The first enantioselective synthesis of trans-6aS,11aR-pterocarpan and its conversion to cis-6aS,11aS -ptarocarpan was also presented starting from racemic 2'-benzyloxyflavanone. Their stereochemistry was deduced by circular dichroism (CD) as well as by X-ray analysis of the ketal intermediate.

Catalytic enantioselective synthesis of indolizino[8,7-b]indole alkaloid derivatives based on the tandem reaction of tertiary enamides

2021 ◽  
Author(s):  
Xin-Ming Xu ◽  
Ming Xie ◽  
Jiazhu Li ◽  
Mei-Xiang Wang
Keyword(s):  
Indole Alkaloid ◽  
Enantioselective Synthesis ◽  
High Yield ◽  
Tandem Reaction ◽  
Indole Derivatives

An exquisite Pybox/Cu(OTf)2-catalyzed asymmetric tandem reaction of tertiary enamides was developed, which enabled the expeditious synthesis of indolizino[8,7-b]indole derivatives in high yield, excellent enantioselectivity and diastereoselectivity.

Synthesis of Axially Chiral 2,2’-Bisphosphobiarenes via a Nickel-Catalyzed Asymmetric Ullmann Coupling: General Access to Privileged Chiral Ligands without Optical Resolution

2020 ◽  
Author(s):  
Ziqing Zuo ◽  
Raphael Kim ◽  
Donald Watson
Keyword(s):  
Optical Resolution ◽  
Chiral Ligands ◽  
Chiral Auxiliaries ◽  
Axially Chiral ◽  
Ullmann Coupling

<div><p>We report an asymmetric Ullmann-type homocoupling of <i>ortho-</i>(iodo)arylphosphine oxides and <i>ortho</i>-(iodo)arylphosphonates that results in highly enantioenriched axially chiral bisphosphine oxides and bisphosphonates in good yields and excellent enantioselectivities. These products are readily converted to enantioenriched biaryl bisphosphines without need for chiral auxiliaries or optical resolution. This process provides a straightforward and practical route for the development of previously uninvestigated atroposelective biaryl bisphosphine ligands.</p></div>

Enantioselective Synthesis of Azamerone

2018 ◽  
Author(s):  
Matthew L. Landry ◽  
Grace McKenna ◽  
Noah Burns
Keyword(s):  
Late Stage ◽  
Cross Coupling ◽  
Enantioselective Synthesis ◽  
Selective Synthesis

A concise and selective synthesis of the dichlorinated meroterpenoid azamerone is described. The paucity of tactics for the synthesis of chiral organochlorides motivated the development of unique strategies for accessing these motifs in enantioenriched forms. The route features a novel enantioselective chloroetherification reaction, a Pd-catalyzed cross-coupling between a quinone diazide and a boronic hemiester, and a late-stage tetrazine [4+2]-cycloaddition/oxidation cascade.

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