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1 article(s) from Huang, Guozheng

Unconventional application of the Mitsunobu reaction: Selective flavonolignan dehydration yielding hydnocarpins

Guozheng Huang,
Simon Schramm,
Jörg Heilmann,
David Biedermann,
Vladimír Křen and
Michael Decker

Beilstein J. Org. Chem. 2016, 12, 662–669, doi:10.3762/bjoc.12.66

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Figure 1: Structures of silibinin, isosilybin, and silychristin, and hydnocarpin-type flavonolignans.

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Figure 2: Synthetic strategy of semi-synthesis of hydnocarpins from silybins [22].

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Scheme 1: Synthesis of ester derivatives of silibinin and conversion to hydnocarpin-type compounds. Reaction ...

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Figure 3: Putative mechanism of dehydration of flavanonols under Mitsunobu conditions.

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Scheme 2: Attempt to dehydrate catechin. Reagents and conditions: a) p-nitrobenzoic acid, Ph₃P, DIAD, THF, rt...

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Scheme 3: Preparation of hydnocarpin (4) and isohydnocarpin (6) and attempt to dehydrate silydianin A (11). R...

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Published 08 Apr 2016

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