A flexible approach to the construction of the C-​20 retinoid carbon skeleton involving the intermol. [3 + 2] cycloaddn. of the nitriles oxide I derived from a C-​14 aldehyde component with (E)​-​HC≡CCMe:CHCH2OAc or (E,​E)​-​CH2:CHCMe:CHCH2OAc, followed by Mo(CO)​6-​promoted ring opening of the derived 3,​5-​disubstituted isoxazoline or isoxazole ring systems, has been accomplished. The same strategy has been also successfully applied as a tool for the crucial carbon-​carbon bond forming step to the formal synthesis of (±)​-​ascofuranone and to a new synthesis of geiparvarin.

Application of [3 + 2] nitrile oxide cycloaddition chemistry to the construction of retinoid skeleton and to a new formal synthesis of (±)-ascofuranone and geiparvarin

BARALDI, Pier Giovanni;MANFREDINI, Stefano;POLLINI, Gian Piero;SIMONI, Daniele
1993

Abstract

A flexible approach to the construction of the C-​20 retinoid carbon skeleton involving the intermol. [3 + 2] cycloaddn. of the nitriles oxide I derived from a C-​14 aldehyde component with (E)​-​HC≡CCMe:CHCH2OAc or (E,​E)​-​CH2:CHCMe:CHCH2OAc, followed by Mo(CO)​6-​promoted ring opening of the derived 3,​5-​disubstituted isoxazoline or isoxazole ring systems, has been accomplished. The same strategy has been also successfully applied as a tool for the crucial carbon-​carbon bond forming step to the formal synthesis of (±)​-​ascofuranone and to a new synthesis of geiparvarin.
1993
Baraldi, Pier Giovanni; Bigoni, Angelica; Guarneri, Mario; Manfredini, Stefano; Pollini, Gian Piero; Simoni, Daniele
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/11392/460438
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