Organic Reactions in Aqueous Media. Cyclopentadienylindium(I) as the First Example of Organoindium(I) Reagent for Carbon−Carbon Bond Formation and the Demonstration of One-Pot Tandem Addition/Intramolecular Diels−Alder Reaction in Aqueous Media

2000 ◽  
Vol 122 (2) ◽  
pp. 402-403 ◽  
Author(s):  
Yang ◽  
Tak Hang Chan
Keyword(s):  
Bond Formation ◽  
Aqueous Media ◽  
Alder Reaction ◽  
Diels Alder ◽  
Organic Reactions ◽  
One Pot ◽  
Carbon Bond ◽  
Diels Alder Reaction ◽  
Carbon Carbon Bond

scholarly journals Studies Towards the Synthesis of Salvinorin A

2006 ◽  
Vol 59 (5) ◽  
pp. 340 ◽  
Author(s):  
Anthony R. Lingham ◽  
Helmut M. Hügel ◽  
Trevor J. Rook
Keyword(s):  
Stereoselective Synthesis ◽  
Aqueous Media ◽  
Alder Reaction ◽  
Diels Alder ◽  
Ring Closure ◽  
Salvinorin A ◽  
One Pot ◽  
Diels Alder Reaction ◽  
Opioid Receptor Agonist ◽  
Ether Bridge

Salvinorin A 1, a psychoactive neoclerodane diterpenoid from the Mexican sage S. divinorum, has gained interest as a selective κ-opioid receptor agonist. Non-racemic 3-furylamines 9a and 9b have been prepared from (+)-pseudoephedrine and (–)-ephedrine for application in the stereoselective synthesis of the ketone ring of 1. Diels–Alder reaction of 9b with methyl acrylate in aqueous media, followed by selective ether bridge cleavage, has allowed access to the cyclohexenone 17 with preservation of stereochemistry at C2. A model route to the lactone ring has also been achieved through a one-pot deconjugation/esterification procedure of 2-bromocrotonyl chloride 20 to the furyl alcohol 19 followed by Reformatski-mediated ring closure.

scholarly journals Correlation between carbon–carbon bond length and the ease of retro Diels–Alder reaction

2014 ◽  
Vol 126 (5) ◽  
pp. 1369-1371 ◽  
Author(s):  
SAMBASIVARAO KOTHA ◽  
SHAIBAL BANERJEE ◽  
MOBIN SHAIKH
Keyword(s):  
Bond Length ◽  
Alder Reaction ◽  
Diels Alder ◽  
Carbon Bond ◽  
Diels Alder Reaction ◽  
Carbon Carbon Bond
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