One-Pot Cascade Synthesis of Fused Nitrogen-Containing Heterocycles in Aqueous Media – Utility of N-Protective Groups in Intramolecular Diels–Alder Reaction of Furan

Synthesis ◽  
2016 ◽  
Vol 48 (17) ◽  
pp. 2873-2880 ◽  
Author(s):  
Aydin Demircan ◽  
Muhammet Kandemir ◽  
Medine Colak ◽  
Muhsin Karaarslan
Keyword(s):  
Aqueous Media ◽  
Alder Reaction ◽  
Diels Alder ◽  
One Pot ◽  
Diels Alder Reaction ◽  
Protective Groups

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.

Aza-Diels-Alder Reaction Between 1,2-Diaza-1,3-dienes and β-Aryl-α,β-unsaturated Carbonyl Compounds. Easy One-pot Entry to 2’-Oxo-imidazo[1’,5’- f]tetrahydropyridazine

2014 ◽  
Vol 10 (6) ◽  
pp. 951-960
Author(s):  
Orazio Attanasi ◽  
Luca Bianchi ◽  
Maurizio D’Auria ◽  
Gianfranco Favi ◽  
Fabio Mantellini ◽  
...  
Keyword(s):  
Carbonyl Compounds ◽  
Alder Reaction ◽  
Diels Alder ◽  
One Pot ◽  
Diels Alder Reaction

scholarly journals Studies on the transannular Diels–Alder reaction of 15-membered macrocyclic trienes containing a trans-trans diene. Part I: Synthesis and isomerization of various model cyclopentadecatrienes

1995 ◽  
Vol 73 (10) ◽  
pp. 1675-1694 ◽  
Author(s):  
Dennis G. Hall ◽  
Renate Müller ◽  
Pierre Deslongchamps
Keyword(s):  
Aqueous Media ◽  
Alder Reaction ◽  
Membered Ring ◽  
Diels Alder ◽  
Coupling Reactions ◽  
Diels Alder Reaction ◽  
Trans Diene

The transannular Diels–Alder reaction of 15-membered macrocyclic trienes with a trans-trans-cis (TTC) olefin geometry can lead to A.B.C.[6.6.7] tricyclic products of trans-syn-trans (TST) and cis-syn-cis (CSC) stereochemistry whereas the TTT isomers can produce the trans-anti-cis (TAC) and cis-anti-trans (CAT) tricycles. In order to study the influence of the position (pro-6.6 or pro-6.7) and the nature (alkyl, alkoxymethyl, or formyl) of the dienophile substituent, a set of 10 model cyclopentadecatrienes was prepared. The synthesis of appropriately functionalized trisubstituted dienophile and diene synthons, as well as their coupling reactions affording acyclic precursors, is described in this paper (first in a series of two). A mild and efficient macrocyclization protocol yielded the required methyl- or alkoxymethyl-substituted cyclic substrates. Further transformations led to the formyl-substituted ones. In particular, the TTT macrocycles containing an enal as a dienophile could be completely isomerized to the corresponding TTC thermodynamic isomers in acidic aqueous media. Keywords: transannular, Diels–Alder, 15-membered ring, A.B.C.[6.6.7] tricycles, diterpene.

Intramolecular hetero-Diels–Alder reaction of 1-oxa-1,3-butadienes with terminal acetylenes in aqueous media using CuI

Tetrahedron ◽  
2008 ◽  
Vol 64 (48) ◽  
pp. 10924-10929 ◽  
Author(s):  
Malihe Javan Khoshkholgh ◽  
Saeed Balalaie ◽  
Rolf Gleiter ◽  
Frank Rominger
Keyword(s):  
Aqueous Media ◽  
Alder Reaction ◽  
Diels Alder ◽  
Diels Alder Reaction ◽  
Terminal Acetylenes
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