A protocol is presented for a completely enantioselective formal desymmetrization of Cs-symmetric diols by monoprotection of the corresponding enantiopure C2 diols, followed by an inversion of configuration by a Mitsunobu reaction (“Mitsunobu trick”). Its application to the unprecedented synthesis of enantiopure cis-3,4-dihydroxypyrroline N-oxides, employed in the enantiodivergent synthesis of two selectively protected 1,2,7-trihydroxyindolizidines, is also reported.
Formal Desymmetrization via a "Mitsunobu Trick". Enantiomerically Pure cis-3,4-Dihydroxypyrroline N-Oxides for the Enantiodivergent Synthesis of Trihydroxyindolizidines / S. Cicchi; J. Nunes Jr.; A. Goti; A. Brandi. - In: EUROPEAN JOURNAL OF ORGANIC CHEMISTRY. - ISSN 1434-193X. - STAMPA. - 1998:(1998), pp. 419-421.
Formal Desymmetrization via a "Mitsunobu Trick". Enantiomerically Pure cis-3,4-Dihydroxypyrroline N-Oxides for the Enantiodivergent Synthesis of Trihydroxyindolizidines
CICCHI, STEFANO;GOTI, ANDREA;BRANDI, ALBERTO
1998
Abstract
A protocol is presented for a completely enantioselective formal desymmetrization of Cs-symmetric diols by monoprotection of the corresponding enantiopure C2 diols, followed by an inversion of configuration by a Mitsunobu reaction (“Mitsunobu trick”). Its application to the unprecedented synthesis of enantiopure cis-3,4-dihydroxypyrroline N-oxides, employed in the enantiodivergent synthesis of two selectively protected 1,2,7-trihydroxyindolizidines, is also reported.File | Dimensione | Formato | |
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