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2 article(s) from Carvalho, M Fernanda N N

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

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Scheme 1: Synthesis of 3-oxo-camphorsulfonylimine (3) [13,15] and its bis-alkynyl derivatives 4 from camphor-10-sulf...

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Scheme 2: Reactions of bis-alkynyl camphor derivative 4a with TiCl₄ and with Br₂, respectively.

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Scheme 3: Reactions of bis-alkynylcamphor derivatives 4a–e with catalytic amounts of PtCl₂(PhCN)₂.

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Scheme 4: Attempted selective synthesis of 3-alkynyl derivatives via sulfonylimine reduction of oxoimide 3.

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Scheme 5: Selective synthesis of 2-alkynyl derivatives by protection of the 3-oxo group as an acetal.

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Scheme 6: Selective synthesis of 2-alkynyl derivatives by protection of the 3-oxo group as an imine.

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Scheme 7: Synthesis of the bis-alkynyl derivatives bearing different alkyne substituents and their platinum-c...

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Scheme 8: Proposed mechanism of the platinum-catalysed cycloisomerisation.

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Published 26 Jun 2017

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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

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Figure 1: Camphor and some camphor derivatives.

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Scheme 1: Formation of 2 from reaction of oxoimine 1 with amino acids (H₂NCH(R)COOH: R = H, CH₃, CH₂Ph, CH₂CH...

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Figure 2: ESI mass spectrum of 2 (positive ion mode).

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Figure 3: ¹H NMR spectrum of 2 in CD₃CN at T = −20 °C.

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Figure 4: ¹³C NMR spectrum of 2 in CD₃CN at T = −20 °C.

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Figure 5: Optimized structure of 2 ((S)-3A isomer) with labeling scheme.

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Figure 6: NOESY spectrum (detail) showing the cross peak between H3A and H10A (see Supporting Information File 1, Figure S6 for the full s...

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Figure 7: Upper row: anion 3 and zwitterion 4 which are stable upon geometry optimization. Middle row: zwitte...

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Figure 8: Intramolecular reactions of non-zwitterionic ground state 6g to 11 (top) or 8 (bottom). The activat...

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Figure 9: Transition-state geometry and salient bond distances along the IRC path for the reaction of 6g → 11...

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Figure 10: Transition-state geometry and salient bond distances along the IRC path for the reaction of 6g → 8....

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Figure 11: Potential products 7–11 of the Strecker degradation together with the reaction of compound 10 to gi...

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Figure 12: ESI(+) tandem mass spectrum of the intermediate 12 (m/z 229) and proposed fragment ions.

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Published 18 Apr 2016

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