Synthesis of alkynyl-substituted camphor derivatives and their use in the preparation of paclitaxel-related compounds

• M. Fernanda N. N. Carvalho,
• Rudolf Herrmann and
• Gabriele Wagner

Beilstein J. Org. Chem. 2017, 13, 1230–1238, doi:10.3762/bjoc.13.122

• electrophilic than that of the C=O bond. However, with bulkier alkynes (e.g., 1-adamantylacetylene or 1-methoxy-1-ethynylcyclohexane), an attack at the carbonyl group becomes more pronounced. Presumably, the C=O carbon atom in 3-oxo-camphorsulfonylimine is sterically more accessible, whereas the sulfonylimine C

• cycloisomerisations and help to clarify the role of the substituents, but also yields a novel type of taxoid compounds of complex polycyclic structures with potential biological effects. Synthesis of 3-oxo-camphorsulfonylimine (3) [13][15] and its bis-alkynyl derivatives 4 from camphor-10-sulfonic acid (1). Reactions

Strecker degradation of amino acids promoted by a camphor-derived sulfonamide

• M. Fernanda N. N. Carvalho,
• M. João Ferreira,
• Ana S. O. Knittel,
• Maria da Conceição Oliveira,
• João Costa Pessoa,
• Rudolf Herrmann and
• Gabriele Wagner

Beilstein J. Org. Chem. 2016, 12, 732–744, doi:10.3762/bjoc.12.73

• developed by means of DFT calculations on potential transition states. Keywords: amino acids; camphorsulfonylimine; DFT calculations; NMR characterization; Strecker degradation; Introduction Among the many derivatives of natural camphor, oxoimine 1 (Figure 1) shows an especially versatile chemistry. The C