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2 article(s) from Brüdgam, Irene

Highly substituted benzannulated cyclooctanol derivatives by samarium diiodide-induced cyclizations

Jakub Saadi,
Irene Brüdgam and
Hans-Ulrich Reissig

Beilstein J. Org. Chem. 2010, 6, 1229–1245, doi:10.3762/bjoc.6.141

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Scheme 1: SmI₂-induced cyclizations of styryl-substituted γ-ketoesters A to benzannulated cyclooctanol deriva...

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Scheme 2: Three-step synthesis of precursor 4 starting from siloxycyclopropane derivative 1.

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Scheme 3: Attempted cyclizations of diastereomeric cycloheptanone derivatives 5a and 5b.

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Scheme 4: Samarium diiodide-induced cyclization of γ-ketoester 7a to tricyclic compound 8.

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Scheme 5: Samarium diiodide-induced cyclizations of methyl ketone 4 and iso-propyl ketone 11.

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Figure 1: NOESY-correlation for compound 10.

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Figure 2: NOESY-correlation for compound 9.

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Scheme 6: Assumed transition structures and intermediates A, B, or C for the cyclizations of (2-propenyl)phen...

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Scheme 7: Reductive fragmentation of highly hindered ketoester 14.

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Scheme 8: Samarium diiodide-induced cyclization of phenyl-substituted substrate 16 leading to lactones 17a an...

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Figure 3: Molecular structure (Diamond [52]) of compound 17b.

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Scheme 9: Samarium diiodide-induced cyclizations of (E)-(1-propenyl)phenyl-substituted γ-ketoesters 18, 21, a...

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Figure 4: Proposed transition structure for the cyclization of (E)-1-propenyl-substituted substrates (HMPA li...

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Scheme 10: Attempted samarium diiodide-induced cyclizations with (E)-1-propenyl-substituted precursors 26a and ...

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Scheme 11: Attempted samarium diiodide-induced cyclization of (Z)-1-propenyl-substituted precursor 30.

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Scheme 12: Samarium diiodide-induced cyclizations of γ-ketoesters 33 and 36.

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Scheme 13: Samarium diiodide-induced cyclizations of diastereomeric stilbenyl-substituted γ-ketoesters 38a and ...

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Figure 5: Molecular structure (Diamond [52]) of compound 40.

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Scheme 14: Attempted cyclization of β-dialkyl-substituted styrene derivative 41.

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Scheme 15: Typical products of samarium diiodide-induced 8-endo-trig cyclizations of α-styryl-substituted γ-ke...

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Scheme 16: Typical products of samarium diiodide-induced 8-endo-trig cyclizations of β-styryl-substituted γ-ke...

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Published 28 Dec 2010

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Preparation of pyridine-3,4-diols, their crystal packing and their use as precursors for palladium-catalyzed cross-coupling reactions

Tilman Lechel,
Irene Brüdgam and
Hans-Ulrich Reissig

Beilstein J. Org. Chem. 2010, 6, No. 42, doi:10.3762/bjoc.6.42

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Scheme 1: Deprotection of 3-alkoxypyridinols 1 to pyridine-3,4-diols 2. ^aMethod a: Pd/C, H₂, MeOH, rt, 1 d; ^b...

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Figure 1: X-ray crystal structure of compound 2c/2c′.

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Scheme 2: Conversion of pyridine-3,4-diols 2 into pyridinediyl bistriflates or -nonaflates 3. a) Et₃N, Rf₂O, ...

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Scheme 3: Sonogashira couplings of pyridinediyl bis(perfluoroalkanesulfonates) 3. a) Pd(PPh₃)₄ [or Pd(OAc)₂/P...

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Figure 2: Absorption and fluorescence spectra of compounds 4b and 4c.

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Published 29 Apr 2010

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