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1 article(s) from Chrzanowska, Maria

Synthesis of new substituted 7,12-dihydro-6,12-methanodibenzo[c,f]azocine-5-carboxylic acids containing a tetracyclic tetrahydroisoquinoline core structure

Agnieszka Grajewska,
Maria Chrzanowska and
Wiktoria Adamska

Beilstein J. Org. Chem. 2021, 17, 2511–2519, doi:10.3762/bjoc.17.168

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Graphical Abstract

Figure 1: Natural isopavine alkaloids and synthetic derivatives of isopavine.

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Figure 2: The structure and numbering of dihydromethanodibenzoazocine.

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Scheme 1: The Petasis reaction and the Pomeranz–Fritsch–Bobbitt cyclization.

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Scheme 2: The synthesis of 7,12-dihydro-6,12-methanodibenzo[c,f]azocine-5-carboxylic acids via a combination ...

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Scheme 3: Synthesis of N-benzylated aminoacetaldehyde acetals 3a–e. Conditions: a) reaction run in EtOH; b) r...

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Scheme 4: Synthesis of amino acids 6a–g.

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Scheme 5: Synthesis of dihydromethanodibenzoazocine-5-carboxylic acids 7a–f. Conditions: a) 20% HCl, rt, 24 h...

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Scheme 6: Synthesis of TA-073.

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Scheme 7: Reaction of 6a with 4% aqueous HCl solution in THF and with 20% aqueous HCl solution. Conditions: a...

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Scheme 8: Three pathways of the synthesis of 12, the decarboxylated analogue of 6a.

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Scheme 9: The chemical behavior of 12 in 4% aqueous HCl solution in THF and in 20% aqueous HCl solution.

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Scheme 10: A plausible mechanism of the reaction of 6a with 4% aqueous HCl solution in THF.

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Published 07 Oct 2021

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