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.File in questo prodotto:
Non ci sono file associati a questo prodotto.
I documenti in SFERA sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.
