Tandem Intramolecular Diels-Alder/1,3-Dipolar Cycloaddition Cascade of 1,3,4-Oxadiazoles: Initial Scope and Applications

Accounts of Chemical Research
Justin E Sears, Dale L Boger

Abstract

A summary of the development and initial studies on the scope of a powerful tandem intramolecular [4 + 2]/[3 + 2] cycloaddition cascade of 1,3,4-oxadiazoles is detailed and provides the foundation for its subsequent use in organic synthesis. Implemented with substrates in which both the initiating dienophile and subsequent dipolarophile are tethered to the 1,3,4-oxadiazoles, the studies expanded the scope of oxadiazoles that participate in the reaction cascade, permitted the use of differentiated dienophiles and dipolarophiles, extended their use to unsymmetrical dienophiles and dipolarophiles, provided exclusive control of the cycloaddition regioselectivities, and imposed exquisite control on the cycloaddition stereochemistry. As key reactivity and stereochemical features of the reactions were being defined, the cascade cycloaddition reaction was implemented in the total synthesis of a series of alkaloids including (-)-vindoline, (-)-vindorosine, the closely related natural products (+)-4-desacetoxyvindoline and (+)-4-desacetoxyvindorosine, natural minovine, (+)-N-methylaspidospermidine, (+)-spegazzinine, (-)-aspidospermine, and a number of key analogues. Most recently, it was used in the divergent total syntheses of (+)-fendl...Continue Reading

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Citations

Jun 23, 2016·The Journal of Organic Chemistry·Brian GoldRonald T Raines
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Jul 3, 2019·Accounts of Chemical Research·Xiao-Yu Liu, Yong Qin
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Nov 19, 2020·The Journal of Organic Chemistry·Xianhuang ZengDale L Boger
Sep 17, 2019·Journal of the American Chemical Society·Zhi-Chen Wu, Dale L Boger
Sep 10, 2021·The Journal of Organic Chemistry·Ryan E QuiñonesDale L Boger

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