The asymmetric synthesis of a set of hydroxyphenyl γ-valerolactones was achieved starting from 2-silyloxyfuran and alkoxy-substituted benzaldehydes as common precursors. Key synthesis steps included an enantioselective vinylogous Mukaiyama aldol reaction and a Barton–McCombie deoxygenation. Five enantioenriched γ-valerolactone targets were obtained in 5–6 steps, 18–63% overall yields and 82–98 % ee, paving the way for the straightforward entry to this class of biologically effective and poorly available flavan-3-ol metabolites. In parallel, an unprecedented one-pot reductive ring expansion process was fortuitously discovered, yielding racemic δ-lactone analogues from phenolic butanolide precursors.

Catalytic, Enantioselective Vinylogous Mukaiyama Aldol Reaction of Furan-Based Dienoxy Silanes: A Chemodivergent Approach to γ-Valerolactone Flavan-3-ol Metabolites and δ-Lactone Analogues / Curti, Claudio; Brindani, Nicoletta; Battistini, Lucia; Sartori, Andrea; Pelosi, Giorgio; MENA PARRENO, Pedro Miguel; Brighenti, Furio; Zanardi, Franca; DEL RIO, Daniele. - In: ADVANCED SYNTHESIS & CATALYSIS. - ISSN 1615-4150. - 357:(2015), pp. 4082-4092. [10.1002/adsc.201500705]

Catalytic, Enantioselective Vinylogous Mukaiyama Aldol Reaction of Furan-Based Dienoxy Silanes: A Chemodivergent Approach to γ-Valerolactone Flavan-3-ol Metabolites and δ-Lactone Analogues

CURTI, Claudio;BRINDANI, Nicoletta;BATTISTINI, Lucia;SARTORI, Andrea;PELOSI, Giorgio;MENA PARRENO, Pedro Miguel;BRIGHENTI, Furio;ZANARDI, Franca;DEL RIO, Daniele
2015-01-01

Abstract

The asymmetric synthesis of a set of hydroxyphenyl γ-valerolactones was achieved starting from 2-silyloxyfuran and alkoxy-substituted benzaldehydes as common precursors. Key synthesis steps included an enantioselective vinylogous Mukaiyama aldol reaction and a Barton–McCombie deoxygenation. Five enantioenriched γ-valerolactone targets were obtained in 5–6 steps, 18–63% overall yields and 82–98 % ee, paving the way for the straightforward entry to this class of biologically effective and poorly available flavan-3-ol metabolites. In parallel, an unprecedented one-pot reductive ring expansion process was fortuitously discovered, yielding racemic δ-lactone analogues from phenolic butanolide precursors.
2015
Catalytic, Enantioselective Vinylogous Mukaiyama Aldol Reaction of Furan-Based Dienoxy Silanes: A Chemodivergent Approach to γ-Valerolactone Flavan-3-ol Metabolites and δ-Lactone Analogues / Curti, Claudio; Brindani, Nicoletta; Battistini, Lucia; Sartori, Andrea; Pelosi, Giorgio; MENA PARRENO, Pedro Miguel; Brighenti, Furio; Zanardi, Franca; DEL RIO, Daniele. - In: ADVANCED SYNTHESIS & CATALYSIS. - ISSN 1615-4150. - 357:(2015), pp. 4082-4092. [10.1002/adsc.201500705]
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/11381/2796976
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