Retro-Mannich Reactions of 3-Alkyl-3,4-dihydro-2H-1,3-benz[e]oxazines and the Synthesis of Axially Chiral Resorcinarenes.

ChemInform ◽  
2003 ◽  
Vol 34 (27) ◽  
Author(s):  
Philip C. Bulman Page ◽  
Harry Heaney ◽  
Matthew J. McGrath ◽  
Edward P. Sampler ◽  
Robert F. Wilkins
Keyword(s):  
Mannich Reactions ◽  
Axially Chiral

scholarly journals anti-Selective Direct Asymmetric Mannich Reactions Catalyzed by Axially Chiral Amino Sulfonamide as an Organocatalyst.

ChemInform ◽  
2006 ◽  
Vol 37 (13) ◽  
Author(s):  
Taichi Kano ◽  
Yukako Yamaguchi ◽  
Osamu Tokuda ◽  
Keiji Maruoka
Keyword(s):  
Mannich Reactions ◽  
Axially Chiral

Retro-Mannich reactions of 3-alkyl-3,4-dihydro-2H-1,3-benz[e]oxazines and the synthesis of axially chiral resorcinarenes

2003 ◽  
Vol 44 (14) ◽  
pp. 2965-2970 ◽  
Author(s):  
Philip C.Bulman Page ◽  
Harry Heaney ◽  
Matthew J. McGrath ◽  
Edward P. Sampler ◽  
Robert F. Wilkins
Keyword(s):  
Mannich Reactions ◽  
Axially Chiral

anti-Selective Direct Asymmetric Mannich Reactions Catalyzed by Axially Chiral Amino Sulfonamide as an Organocatalyst

2005 ◽  
Vol 127 (47) ◽  
pp. 16408-16409 ◽  
Author(s):  
Taichi Kano ◽  
Yukako Yamaguchi ◽  
Osamu Tokuda ◽  
Keiji Maruoka
Keyword(s):  
Mannich Reactions ◽  
Axially Chiral

Total Synthesis of Axially-Chiral Cannabinols: A New Platform for Cannabinoid-Based Drug Discovery

2019 ◽  
Author(s):  
Primali Navaratne ◽  
Jenny Wilkerson ◽  
Kavindri Ranasinghe ◽  
Evgeniya Semenova ◽  
Lance McMahon ◽  
...  
Keyword(s):  
Drug Discovery ◽  
Total Synthesis ◽  
Ground State ◽  
Chemical Space ◽  
Modern Medicine ◽  
The Novel ◽  
Pharmaceutical Development ◽  
Bioactive Component ◽  
Axially Chiral ◽  
New Directions

<div> <div> <div> <p>Phytocannabinoids, molecules isolated from cannabis, are gaining attention as promising leads in modern medicine, including pain management. Considering the urgent need for combating the opioid crisis, new directions for the design of cannabinoid-inspired analgesics are of immediate interest. In this regard, we have hypothesized that axially-chiral-cannabinols (ax-CBNs), unnatural (and unknown) isomers of cannabinol (CBN) may be valuable scaffolds for cannabinoid-inspired drug discovery. There are multiple reasons for thinking this: (a) ax-CBNs would have ground-state three-dimensionality akin to THC, a key bioactive component of cannabis, (b) ax-CBNs at their core structure are biaryl molecules, generally attractive platforms for pharmaceutical development due to their ease of functionalization and stability, and (c) atropisomerism with respect to phytocannabinoids is unexplored “chemical space.” Herein we report a scalable total synthesis of ax-CBNs, examine physical properties experimentally and computationally, and provide preliminary behavioral and analgesic analysis of the novel scaffolds. </p> </div> </div> </div>

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