1.2 Cation–π Cyclizations of Epoxides and Polyepoxides

K. W. Armbrust; T. Halkina; E. H. Kelley; S. Sittihan; T. Jamison

doi:10.1055/sos-SD-219-00044

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Snyder, S. A.: 2016 Science of Synthesis, 2015/4a: Applications of Domino Transformations in Organic Synthesis 1 DOI: 10.1055/sos-SD-219-00044

Applications of Domino Transformations in Organic Synthesis 1

1.2 Cation–π Cyclizations of Epoxides and Polyepoxides

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Editor: Snyder, S. A.

Authors: Adu-Ampratwum, D.; Anderson, E.; Armbrust, K. W.; Devery, J.; Douglas, J.; Doyle, M. P.; Engle, K. M.; Forsyth, C. J.; Gille, F.; Halkina, T.; Hu, X.; Jamison, T.; Kelley, E. H.; Kirschning, A.; Lee, D.; Maimone, T.; Merino, E.; Nevado Blazquez, C.; O'Connor, M. J.; Ohshima, T.; Parker, K.; Renata, H.; Salvador, A.; Schaumann, E.; Shenvi, R.; Shi, L.-L.; Sittihan, S.; Snyder, S. A.; Stephenson, C. R. J.; Tang, M.; Truong, P.; Tu, Y.-Q.; Wan, K.; Wang, S.-H.; Wolling, M.; Xu, X.; Yang, Z.

Title: Applications of Domino Transformations in Organic Synthesis 1

Print ISBN: 9783131731319; Online ISBN: 9783132402522; Book DOI: 10.1055/b-003-128286

1st edition © 2016. Thieme. All rights reserved.
Georg Thieme Verlag KG, Stuttgart

Subjects: Organic Chemistry;Chemical Reactions, Catalysis;Organometallic Chemistry;Laboratory Techniques, Stoichiometry

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Parent publication

Title: Science of Synthesis

DOI: 10.1055/b-00000101

Series Editors: Carreira, E. M.; Decicco, C. P.; Fürstner, A.; Koch, G.; Molander, G.; Schaumann, E.; Shibasaki, M.; Thomas, E. J.; Trost, B. M.

Type: Multivolume Edition

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Abstract

This chapter describes the formation of complex polycyclic fragments from linear epoxide and polyepoxide precursors via domino reactions. Depending on the reaction conditions employed, either exo or endo epoxide opening can be selectively achieved. Applications of these domino reactions toward the synthesis of complex natural products are discussed.

Key words

oxiranes - cascades - natural products - marine ladder polyethers - ionophores - ethers - oxygen heterocycles - tetrahydrofurans - tetrahydropyrans - oxepanes

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