A formal total synthesis of (+)-tetronolide, the aglycon of the tetrocarcins: enantio-and diastereoselective syntheses of the octahydronaphthalene (bottom-half) and …

WR Roush, ML Reilly, K Koyama…

Index: Roush, William R.; Reilly, Melissa L.; Koyama, Kazuo; Brown, Bradley B. Journal of Organic Chemistry, 1997 , vol. 62, # 25 p. 8708 - 8721

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Citation Number: 74

Abstract

A formal total synthesis of (+)-tetronolide, the aglycon of the tetrocarcins, has been achieved by virtue of the development of highly diastereo-and enantioselective syntheses of the bottom-and top-half fragments 4 and 5 reported herein. These fragments previously served as key intermediates in Yoshii's pioneering total synthesis of (+)-tetronolide. The synthesis of the bottom-half octahydronaphthalene unit 4 features the intramolecular Diels-Alder ...