Domino Reactions That Combine an Azido-Schmidt Ring Expansion with the Diels−Alder Reaction

2004 ◽  
Vol 6 (26) ◽  
pp. 4993-4995 ◽  
Author(s):  
Yibin Zeng ◽  
D. Srinivasa Reddy ◽  
Erin Hirt ◽  
Jeffrey Aubé
Keyword(s):  
Ring Expansion ◽  
Alder Reaction ◽  
Diels Alder ◽  
Domino Reactions ◽  
Diels Alder Reaction

scholarly journals Domino Reactions that Combine an Azido-Schmidt Ring Expansion with the Diels?Alder Reaction.

ChemInform ◽  
2005 ◽  
Vol 36 (17) ◽  
Author(s):  
Yibin Zeng ◽  
D. Srinivasa D. Reddy ◽  
Erin Hirt ◽  
Jeffrey Aube
Keyword(s):  
Ring Expansion ◽  
Alder Reaction ◽  
Diels Alder ◽  
Domino Reactions ◽  
Diels Alder Reaction

scholarly journals Domino reactions in the synthesis of heterocyclic natural products and analogs

2004 ◽  
Vol 76 (11) ◽  
pp. 1967-1983 ◽  
Author(s):  
L. F. Tietze ◽  
N. Rackelmann
Keyword(s):  
Alder Reaction ◽  
Diels Alder ◽  
Domino Reactions ◽  
Complex Molecules ◽  
Enol Ethers ◽  
Dicarbonyl Compound ◽  
Bond Forming ◽  
Enantioselective Total Synthesis ◽  
Subsequent Transformation ◽  
Diels Alder Reaction

Domino reactions are defined as processes of two or more bond-forming reactions under identical conditions, in which the subsequent transformation takes place at the functionalities obtained in the former transformation. They allow the efficient synthesis of complex molecules from simple substrates in an ecologically and economically favorable way. A very powerful domino process is the domino Knoevenagel–hetero-Diels–Alder reaction, in which an aldehyde or an beta-ketoester is condensed with a 1,3-dicarbonyl compound or a heteroanalog to give a 1-oxa-1,3-butadiene, which can undergo an inter- or intramolecular hetero-Diels–Alder reaction with dienophiles such as enol ethers or alkenes. The products are dihydropyrans, which can be transformed in a variety of ways. Thus, an extension of the process is the synthesis of highly substituted pyrrolidines, piperidines, and azepanes using aminoaldehydes. The process has also been employed for the enantioselective total synthesis of a variety of alkaloids, such as indol- and ipecacuanha alkaloids. In another domino process, erythrina and homoerythrina alkaloids have been prepared from simple phenylethylamines and ketoesters.

Diels–Alder approach to (±)-longifolene: A formal synthesis

1992 ◽  
Vol 70 (5) ◽  
pp. 1375-1384 ◽  
Author(s):  
Tse-Lok Ho ◽  
Wen-Lung Yeh ◽  
John Yule ◽  
Hsing-Jang Liu
Keyword(s):  
Maleic Anhydride ◽  
Ring Expansion ◽  
Alder Reaction ◽  
Diels Alder ◽  
Formal Synthesis ◽  
Racemic Form ◽  
Diels Alder Reaction ◽  
Key Steps

A formal synthesis of longifolene in racemic form is concluded starting from the Diels–Alder reaction of 6,6-di-methylfulvene and maleic anhydride. Key steps are cyclodehydration, conjugate methylation, and ring expansion.

A total synthesis of (±)-cedrol and (±)-cedrene via an intramolecular Diels–Alder reaction

1976 ◽  
Vol 54 (12) ◽  
pp. 1991-1993 ◽  
Author(s):  
Edward G. Breitholle ◽  
Alex G. Fallis
Keyword(s):  
Total Synthesis ◽  
Ring Expansion ◽  
Alder Reaction ◽  
Diels Alder ◽  
Diels Alder Reaction

A total synthesis of racemic cedrol and cedrene is described in which a key step is the intramolecular Diels–Alder reaction of alkyl cyclopentadiene 3 to give the tricyclic olefin 4. Oxidation of this material followed by ring expansion gives cedrone (6) which is converted to the sesquiterpenes. Modification of the functionality of the starting materials will permit the application of this general route to diverse tricyclic systems.

Sign in / Sign up

Export Citation Format

Share Document