Interplay of cascade oxidative cyclization and hydride shifts in the synthesis of the ABC spiroketal ring system of pectenotoxin-4

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Abstract

Concepts: The formation of stereochemically defined bis-THF units through a double cyclization and a hydride-shift-initiated route to spiroketals is described (see scheme; Xc=chiral auxiliary). The resulting sequence has been used in a synthesis of the C1-16 fragment of the naturally occurring antitumor agent pectenotoxin-4. Copyright © 2013 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

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Donohoe, T. J., & Lipiński, R. M. (2013). Interplay of cascade oxidative cyclization and hydride shifts in the synthesis of the ABC spiroketal ring system of pectenotoxin-4. Angewandte Chemie - International Edition, 52(9), 2491–2494. https://doi.org/10.1002/anie.201208919

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