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Prof. Timothy J. Donohoe and Radosław M. Lipiński 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

Article first published online: 30 JAN 2013 | DOI: 10.1002/anie.201208919

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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.

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