Beilstein J. Org. Chem.2017,13, 2663–2670, doi:10.3762/bjoc.13.264
analogue of streptopyrrolidine was accomplished in 65% overall yield.
Keywords: azlactones; dimerization; diasteoreselective synthesis; kinetics; streptopyrrolidineanalogue; Findings
Azlactones have been acknowledged as a common nucleophilic reagent to introduce a quaternary carbon stereocenter in the α
(Scheme 3). Compound 2c was dissolved in a mixture of acetic acid and NaBH4, cooled to 0 °C to afford the highly functionalized (+/−)-streptopyrrolidineanalogue 6 in 70% yield as a unique diastereomer. Streptopyrrolidine was isolated from the marine bacterium Streptomyces sp. and has exhibited a
NMR spectroscopic monitoring and revealed that the diastereoselectivity was determined during C–C bond formation step. A diastereoselective streptopyrrolidineanalogue, containing three contiguous stereogenic centers, was smoothly obtained as a sole diastereomer in 70% yield.
Structure of an azlactone