ChemInform Abstract: Synthesis and Transannular Diels-Alder Reaction of a 13-Membered Macrocyclic Triene Having a Tetrasubstituted Enol Ether as Dienophile.

ChemInform ◽  
1990 ◽  
Vol 21 (35) ◽  
Author(s):  
G. BERUBE ◽  
P. DESLONGCHAMPS
Keyword(s):  
Alder Reaction ◽  
Diels Alder ◽  
Enol Ether ◽  
Diels Alder Reaction

Iodine-promoted imino-Diels–Alder reaction of fluorinated imine with enol ether: synthesis of 2-perfluorophenyl tetrahydroquinoline derivatives

Tetrahedron ◽  
2010 ◽  
Vol 66 (4) ◽  
pp. 913-917 ◽  
Author(s):  
Guifang Jin ◽  
Jingwei Zhao ◽  
Jianwei Han ◽  
Shizheng Zhu ◽  
Jianmin Zhang
Keyword(s):  
Alder Reaction ◽  
Diels Alder ◽  
Enol Ether ◽  
Diels Alder Reaction ◽  
Ether Synthesis

Synthesis and transannular Diels–Alder reaction of a 13-membered macrocyclic triene having a tetrasubstituted enol ether as dienophile

1990 ◽  
Vol 68 (3) ◽  
pp. 404-411 ◽  
Author(s):  
Gervais Bérubé ◽  
Pierre Deslongchamps
Keyword(s):  
Organic Synthesis ◽  
Alder Reaction ◽  
Diels Alder ◽  
The Other ◽  
Enol Ether ◽  
Diels Alder Reaction ◽  
Other Hand ◽  
Tricyclic Compounds

The syntheses of the acyclic triene trans–trans–cis27 and trans–trans–trans31 are described. Macrocyclization and concomitant transannular Diels–Alder reaction were performed with the chloride derivative obtained from the trans–trans–cis triene alcohol 27 yielding a mixture of the tricyclic compounds trans–syn–trans33 and cis–syn–cis34. On the other hand, macrocyclization of the chloride derived from trans–trans–trans triene 31 was not successful. Keywords: transannular process, Diels–Alder reaction, macrocyclic triene, macrocyclization, tricyclic compounds, organic synthesis.

Total Synthesis of Lycoposerramine-R

Synlett ◽  
2018 ◽  
Vol 29 (18) ◽  
pp. 2377-2380
Author(s):  
Satoshi Yokoshima ◽  
Shinya Watanabe ◽  
Masatsugu Ishikawa ◽  
Toshimune Nomura ◽  
Tohru Fukuyama
Keyword(s):  
Total Synthesis ◽  
Alder Reaction ◽  
Diels Alder ◽  
Quaternary Carbon ◽  
Enol Ether ◽  
Ethynyl Group ◽  
Diels Alder Reaction

A total synthesis of lycoposerramine-R was accomplished. The synthesis featured a Claisen–Ireland rearrangement to install a two-carbon unit, and a hetero-Diels–Alder reaction to form a cyclic enol ether that reacted with an ethynyl group to construct a cis-hydrindane core containing a quaternary carbon. A 2-pyridone synthesis using 2-(phenylsulfinyl)acetamide was used to complete the synthesis.

Enantioselective Synthesis of Epi-Emetine Analogues: Control of the Facial Selectivity in a Three-Component Domino Knoevenagel-Hetero-Diels-Alder Reaction*

2004 ◽  
Vol 59 (4) ◽  
pp. 468-477 ◽  
Author(s):  
Lutz F. Tietze ◽  
Nils Rackelmann
Keyword(s):  
Main Product ◽  
Enantioselective Hydrogenation ◽  
Alder Reaction ◽  
Diels Alder ◽  
Enantioselective Synthesis ◽  
Enol Ether ◽  
Meldrum’S Acid ◽  
Chiral Catalyst ◽  
Diels Alder Reaction ◽  
Facial Selectivity

AbstractThe domino Knoevenagel-hetero-Diels-Alder reaction of the aldehyde rac-8, Meldrum’s acid 2 and enol ether 3 leads to the cycloadduct rac-17 as the main product which in a second domino process was transformed into the benzoisoquinolizidine rac-18 by solvolysis, hydrogenolysis, condensation and hydrogenation; rac-18 was used as a substrate for the synthesis of the two diastereomeric epiemetine analogues 9 and 10 with > 96% ee (9) and 80% ee (10), respectively, by condensation with the phenylethylamine 23, Bischler-Napieralski reaction and “enantioselective” hydrogenation using the chiral catalyst (R,R)-26.

Development of methods suitable for natural product synthesis: The azadirachtin story

2005 ◽  
Vol 77 (7) ◽  
pp. 1115-1130 ◽  
Author(s):  
Steven V. Ley
Keyword(s):  
Natural Product ◽  
Claisen Rearrangement ◽  
Alder Reaction ◽  
Diels Alder ◽  
Natural Product Synthesis ◽  
Enol Ether ◽  
Ring Contraction ◽  
Left Hand ◽  
Diels Alder Reaction ◽  
Rearrangement Reaction

Our synthesis work on the insect antifeedant azadirachtin is described. Particular emphasis is placed on the key coupling of a left-hand decalin fragment with a right-hand hydroxydihydrofuran acetal unit via a Claisen rearrangement reaction of an intermediate propargylic enol ether. New chemistry has been developed leading to control of an endo-selective intramolecular Diels–Alder reaction using silicon, which was essential for the construction of the appropriately functionalized decalin fragment. In order to install the five-ring hemiacetal of azadirachtin, we also developed a new ring contraction protocol via an intermediate six-ring cyano ester.

Sign in / Sign up

Export Citation Format

Share Document