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• W2149296596 abstract "The structural designation A originally made by Sharma and Alam to sclerophytin A was considered to be ambiguous and so notably strained relative to B that the latter was targeted for de novo synthesis (Scheme 1). Our two successful routes began with (5S)-(d-menthyloxy)-2(5H)-furanone and involved the application of cycloaddition, Claisen ring expansion, transannular oxymercuration, and 1,2-carbonyl transposition tactics to arrive at B. It was immediately apparent from polarity considerations and spectroscopic data that the antileukemic marine metabolite in question was in need of more deep-seated structural revision. Following close re-examination of an acquired authentic sample by advanced NMR techniques, the strong inference was made that sclerophytin A actually lacked a second oxygen bridge and was in reality the triol C. This conclusion was unequivocally confirmed by diverting an advanced intermediate generated earlier into a short sequence beginning with regiocontrolled dihydroxylation and terminating with configurational inversion at the secondary carbinol center. The status of other members of this series is also presented." @default.
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• W2149296596 date "2001-01-01" @default.
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• W2149296596 title "The sclerophytin A adventure" @default.
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• W2149296596 doi "https://doi.org/10.1002/tcr.1016" @default.
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