The Zipper-Mode Domino Intramolecular Diels–Alder Reaction: A New 0→ABCD Strategy for Steroids and Related Compounds We thank Dr. Simon Fielder (HortResearch New Zealand) and Mr. Leon Wong (University of Sydney) for preliminary experiments, Dr. Kelvin Picker (University of Sydney) for assistance with HPLC and GC analyses, and Dr. Ian Luck (University of Sydney) for 2D NMR experiments. This work was supported by The Australian Research Council and The University of Sydney.

Author(s):  
Marck Nörret ◽  
Michael S. Sherburn
Author(s):  
Douglass Taber

José Barluenga of the Universidad de Oviedo described (Organic Lett. 2008, 10, 4469) a powerful route from lithiated arenes such as 1 to the benzocyclobutane 3, the immediate precursor to the powerful o-quinone methide Diels-Alder diene. Michael E. Jung of UCLA developed (Organic Lett. 2008, 10, 3647) a triflimide catalyst for the inverse electron demand coupling of the highly substituted diene 4 with the enol ether 5 to give 6 with high diastereocontrol. Joseph M. Fox of the University of Delaware showed (J. Org. Chem. 2008, 73, 4283) that the cyclopropene carboxylate 8 was a powerful and selective dienophile. Richard P. Hsung and Kevin P. Cole of the University of Wisconsin finally (Adv. Synth. Cat. 2008, 350, 2885) reduced to practice the long-sought enantioselective Diels-Alder cycloaddition of a trisubstituted aldehyde, 11. Li Deng of Brandeis University devised (J. Am. Chem. Soc. 2008, 130, 2422) a Cinchona -derived catalyst for Diels-Alder cycloaddition to the diene 13 with high ee. Miguel Á. Sierra of the Universidad Complutense, Madrid, and Alejandra G. Suárez of the Universidad Nacional de Rosario described (Organic Lett. 2008, 10, 3389) a clever switchable chiral auxiliary 16 that favored diastereomer S-18 on thermal addition, but R-18 with EtAlCl2. New approaches to the intramolecular Diels-Alder reaction continue to be introduced. Mathias Christmann, now at the TU Dortmund, showed (Angew. Chem. Int. Ed. 2008, 47, 1450) that a secondary amine organocatalyst converted the prochiral dialdehyde 19 into the bicyclic diene 20 with high de and ee. Martin G. Banwell of the Australian National University prepared (Organic Lett. 2008, 10, 4465) the triene 21 in high ee by microbiological oxidation of iodobenzene. On warming, 21 was converted smoothly into 22, which was carried on in a formal synthesis of platencin. Jun-ichi Matsuo of Kanazawa University was able (Organic Lett. 2008, 10, 4049) to induce (neat, 180 °C) the intermolecular Diels-Alder cycloaddition of 23 with 24, delivering the cycloadduct 25 with 11:1 diastereocontrol.


1998 ◽  
Vol 39 (19) ◽  
pp. 2977-2980 ◽  
Author(s):  
Toshihiro Hashimoto ◽  
Hiroshi Irita ◽  
Masami Tanaka ◽  
Shigeru Takaoka ◽  
Yoshinori Asakawa

Author(s):  
Hideo Nemoto ◽  
Masami Hashimoto ◽  
Hiroshi Kurobe ◽  
Keiichiro Fukumoto ◽  
Tetsuji Kametani

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