The total synthesis of Lentiginosine (3) is reported. The strategy is based on the 1,3-dipolar cycloaddition of a TBDPS protected 3,4-dihydroxypyrroline N-oxide to methylenecyclopropane followed by the thermal rearrangement of the resulting spirocyclopropaneisoxazolidine to give the functionalised indolizidine skeleton. The compound shows an [alpha](D) value identical, but opposite in sign, with that reported for the natural isomer which has been assigned the same absolute configuration.
Synthesis of Lentiginosine by Stereoselective Chiral Nitrone Cycloaddition and Thermal Rearrangement of Strained Spiroisoxazolidine / F. M. Cordero; S. Cicchi; A. Goti; A. Brandi. - In: TETRAHEDRON LETTERS. - ISSN 0040-4039. - STAMPA. - 35:(1994), pp. 949-952. [10.1016/S0040-4039(00)76008-4]
Synthesis of Lentiginosine by Stereoselective Chiral Nitrone Cycloaddition and Thermal Rearrangement of Strained Spiroisoxazolidine
CORDERO, FRANCA MARIA;CICCHI, STEFANO;GOTI, ANDREA;BRANDI, ALBERTO
1994
Abstract
The total synthesis of Lentiginosine (3) is reported. The strategy is based on the 1,3-dipolar cycloaddition of a TBDPS protected 3,4-dihydroxypyrroline N-oxide to methylenecyclopropane followed by the thermal rearrangement of the resulting spirocyclopropaneisoxazolidine to give the functionalised indolizidine skeleton. The compound shows an [alpha](D) value identical, but opposite in sign, with that reported for the natural isomer which has been assigned the same absolute configuration.I documenti in FLORE sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.