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Beilstein J. Org. Chem. 2021, 17, 2781–2786, doi:10.3762/bjoc.17.188
Graphical Abstract
Figure 1: (−)-Codonopsinol B (1) and its N-nor-methyl analogue 2; known inhibition activities against α-gluco...
Scheme 1: Synthetic approach towards (±)-codonopsinol B (1) and its N-nor-methyl analogue 2.
Scheme 2: Synthesis of isoxazolidine-4,5-diol (±)-3. Reagents and conditions: (a) ᴅʟ-proline, CHCl3, rt, 48 h...
Scheme 3: Synthesis of final pyrrolidines (±)-1 and (±)-2. Reagents and conditions: (a) vinyl-MgBr, CeCl3, TH...
Figure 2: Molecular structure of N-Cbz-protected pyrrolidine 12 confirmed by single-crystal X-ray crystallogr...
Beilstein J. Org. Chem. 2020, 16, 1313–1319, doi:10.3762/bjoc.16.112
Figure 1: 3-Substituted isoxazolidin-4-ols resembling 3-hydroxypyrrolidines.
Scheme 1: Synthetic approach towards isoxazolidin-4-ols via the regioselective reductive cleavage of the C5–O...
Scheme 2: Hydroboration-oxidation of 4,5-unsubstituted 2,3-dihydroisoxazoles.
Figure 2: Selected NOE enhancements observed in the isoxazolidin-4-ol trans-8a. The arrows show the NOESY cor...
Scheme 3: Dess-Martin oxidation of isoxazolidin-4-ols to ketones.
Scheme 4: Inversion of the relative configuration of the isoxazolidine ring.
Figure 3: Selected NOE enhancements observed in the isoxazolidin-4-ol cis-10a. The arrows show the NOESY corr...
Scheme 5: N-debenzylation via N-Troc-protected isoxazolidines.