Nucleophilic addition of aryl Grignard reagents to (2R,3R,4R)-3,4-bis(benzyloxy)-2-(benzyloxymethyl)-3,4-dihydro- 2H-pyrrole 1-oxide afford straightforwardly trihydroxylated pyrrolidine alkaloids. Organometallic additions take place with complete anti selectivity. In order to gain access to all four diastereomers with different configuration at C-2 and C-5, an oxidation– reduction protocol is developed. The high selectivity observed in the nucleophilic addition reaction allowed preparation of natural radicamine B in only two steps and high chemical yield.
Nucleophilic additions and redox reactions of polyhydroxy pyrroline N-oxides en route to pyrrolidine alkaloids. Total synthesis of Radicamine B / P. MERINO; I. DELSO; T. TEJERO; F. CARDONA; A. GOTI. - In: SYNLETT. - ISSN 0936-5214. - STAMPA. - 2007:(2007), pp. 2651-2654. [10.1055/s-2007-991059]
Nucleophilic additions and redox reactions of polyhydroxy pyrroline N-oxides en route to pyrrolidine alkaloids. Total synthesis of Radicamine B
CARDONA, FRANCESCA;GOTI, ANDREA
2007
Abstract
Nucleophilic addition of aryl Grignard reagents to (2R,3R,4R)-3,4-bis(benzyloxy)-2-(benzyloxymethyl)-3,4-dihydro- 2H-pyrrole 1-oxide afford straightforwardly trihydroxylated pyrrolidine alkaloids. Organometallic additions take place with complete anti selectivity. In order to gain access to all four diastereomers with different configuration at C-2 and C-5, an oxidation– reduction protocol is developed. The high selectivity observed in the nucleophilic addition reaction allowed preparation of natural radicamine B in only two steps and high chemical yield.File | Dimensione | Formato | |
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