Synthetic studies on the taxane diterpenes. Utility of the intramolecular Diels-Alder reaction for a single-step, stereocontrolled synthesis of a taxane model system

1983 ◽  
Vol 105 (11) ◽  
pp. 3732-3734 ◽  
Author(s):  
Kunio Sakan ◽  
Bryan M. Craven
Keyword(s):  
Alder Reaction ◽  
Model System ◽  
Single Step ◽  
Diels Alder ◽  
Diels Alder Reaction ◽  
Stereocontrolled Synthesis ◽  
Synthetic Studies

Asymmetric Synthesis of Fused Tetrahydroquinolines via Intramolecular Aza-Diels-Alder Reaction of ortho-Quinone Methide Imines

Synthesis ◽  
2021 ◽  
Author(s):  
Fabian Hofmann ◽  
Cornelius Gärtner ◽  
Martin Kretzschmar ◽  
Christoph Schneider
Keyword(s):  
Asymmetric Synthesis ◽  
Alder Reaction ◽  
Single Step ◽  
Diels Alder ◽  
Quinone Methide ◽  
Bronsted Acid ◽  
Atom Economy ◽  
Diels Alder Reaction ◽  
Brönsted Acid ◽  
Chiral Bronsted Acid

Aza-Diels Alder reactions are straightforward processes in the construction of N-heterocycles, featuring inherent atom-economy and stereospecificity. Intramolecular strategies allow formation of bicyclic core structures with up to three stereocenters within a single step. Herein, this concept is combined with the chemistry of chiral Brønsted acid-bound ortho-quinone methide imines generating a range of interesting fused tetrahydro-quinolines in a diastereo- and enantioselective manner.

Stereo-controlled synthesis of polyheterocycles via the diene-transmissive hetero-Diels–Alder reaction of β,γ-unsaturated α-keto esters

2015 ◽  
Vol 13 (21) ◽  
pp. 5875-5879 ◽  
Author(s):  
Takashi Otani ◽  
Yumiko Tamai ◽  
Kazunori Seki ◽  
Tomohiro Kikuchi ◽  
Taiichiro Miyazawa ◽  
...  
Keyword(s):  
Alder Reaction ◽  
Diels Alder ◽  
Controlled Synthesis ◽  
Keto Esters ◽  
Diels Alder Reaction ◽  
Stereocontrolled Synthesis

Stereocontrolled synthesis of polyheterocycles via the diene-transmissive hetero Diels–Alder reaction of β,χ-unsaturated α-keto esters is described.

scholarly journals Synthetic studies on the bioactive tetramic acid JBIR-22 using a late stage Diels–Alder reaction

2015 ◽  
Vol 13 (42) ◽  
pp. 10527-10531 ◽  
Author(s):  
A. R. Healy ◽  
N. J. Westwood
Keyword(s):  
Late Stage ◽  
Alder Reaction ◽  
Diels Alder ◽  
Tetramic Acid ◽  
Diels Alder Reaction ◽  
Synthetic Studies

A successful late-stage Diels–Alder cyclisation in the synthesis of JBIR-22 highlights it as a viable biosynthetic event.

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