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Beilstein J. Org. Chem. 2025, 21, 526–532, doi:10.3762/bjoc.21.40
Graphical Abstract
Figure 1: A: Structure of cryptophycin-52. B: Cryptophycin-52 derivatives modified with conjugation handles i...
Scheme 1: Synthesis of modified unit B derivatives. a) HNO3, H2SO4, 0 °C, 5 h, 48% (isolated as monohydrate);...
Figure 2: Molecular structure of Boc-ᴅ-Phe(4-NHMe)-OMe 7 as determined by single-crystal X-ray diffraction me...
Scheme 2: Synthesis of cryptophycin diols 24 and 25. a) EDC·HCl, DMAP, NEt3, CH2Cl2, 0 °C to rt, 22 h, 60%; b...
Scheme 3: Three-step diol–epoxide transformation starting from diols 24 and 25. a) (MeO)3CH, pyridinium p-tol...
Beilstein J. Org. Chem. 2017, 13, 2428–2441, doi:10.3762/bjoc.13.240
Figure 1: Concept of carboxylic acid or amide bond replacement on the basis of an alkyne moiety.
Figure 2: Selection of reactions based on propargylamines as precursors. a) Intramolecular Pauson–Khand react...
Figure 3: Two different approaches for the stereoselective de novo synthesis of propargylamines using Ellman’...
Figure 4: Synthesis of propargylamines 4a and 4b by introducing the side chain as nucleophile. (a) HC≡CCH2OH,...
Figure 5: Reaction of N-sulfinylimine 5h with (trimethylsilyl)ethynyllithium. (a) GP-3 or GP-4. (b) Aqueous w...
Figure 6: Side reactions observed in the course of the conversion of highly electrophilic sulfinylimines 5. (...
Figure 7: a) Possible transition states TI and TII for the transfer of the methyl moiety from AlMe3 to the im...
Figure 8: Base-induced rearrangement of propargylamines bearing electron-withdrawing substituents.
Figure 9: Base-catalyzed rearrangement of propargylamines 11 to α,β-unsaturated imines 12. A) Reaction scheme...
Beilstein J. Org. Chem. 2009, 5, No. 43, doi:10.3762/bjoc.5.43
Scheme 1: Selectively cleavable β2-amino acid precursors: Structures and reactivities of 2-tert-butyl-tetrahy...
Scheme 2: Cyclocondensation of Cbz-βAla-NH2 (3) and benzaldehyde. a) [p-TsOH], toluene, reflux, Dean–Stark tr...
Scheme 3: Protection and deprotection of 4. a) Boc2O, DMAP, CH3CN, 16 h, rt; b) 1. n-BuLi, THF, −78 °C, 30 mi...
Scheme 4: Synthesis of enantiopure 2-phenyl-tetrahydropyrimidine-4(1H)-ones. a) PhCH(OMe)2, BF3·Et2O (6.0 equ...
Figure 1: X-ray crystal structure of 10 [44].
Scheme 5: Diastereoselective alkylation of 5.
Figure 2: Comparison of coupling constants (C5–C6-ABX system) within the 1H-NMR spectra of literature known c...
Figure 3: Supposed enolate conformations.
Scheme 6: Selective ring opening of the heterocycle 11d and isolation of orthogonally protected β2-homoaspart...