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2 article(s) from Kouklovsky, Cyrille

Total synthesis of grayanane natural products

Nicolas Fay,
Rémi Blieck,
Cyrille Kouklovsky and
Aurélien de la Torre

Beilstein J. Org. Chem. 2022, 18, 1707–1719, doi:10.3762/bjoc.18.181

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Graphical Abstract

Figure 1: General structure of grayanane natural products.

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Scheme 1: Grayanane biosynthesis.

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Scheme 2: Matsumoto’s relay approach.

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Scheme 3: Shirahama’s total synthesis of (–)-grayanotoxin III.

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Scheme 4: Newhouse’s syntheses of fragments 25 and 29.

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Scheme 5: Newhouse’s total synthesis of principinol D.

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Scheme 6: Ding’s total synthesis of rhodomolleins XX and XXII.

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Scheme 7: First key step of Luo’s strategy.

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Scheme 8: Luo’s total synthesis of grayanotoxin III.

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Scheme 9: Synthesis of principinol E and rhodomollein XX.

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Scheme 10: William’s synthetic effort towards pierisformaside C.

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Scheme 11: Hong’s synthetic effort towards rhodojaponin III.

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Scheme 12: Recent strategies for grayanane synthesis.

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Album

Review

Published 12 Dec 2022

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Preparation of an advanced intermediate for the synthesis of leustroducsins and phoslactomycins by heterocycloaddition

Anaïs Rousseau,
Guillaume Vincent and
Cyrille Kouklovsky

Beilstein J. Org. Chem. 2022, 18, 1385–1395, doi:10.3762/bjoc.18.143

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Graphical Abstract

Figure 1: Structures of leustroducsins and phoslactomycins.

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Figure 2: Synthetic strategy for the leustroducins and phoslactomycins.

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Figure 3: strategy for the synthesis of central fragment 4: nitroso Diels–Alder reaction.

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Scheme 1: A highly regio-and stereoselective nitroso Diels–Alder cycloaddition between Wightman’s reagent 6 a...

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Scheme 2: Hydrolysis of enol phosphate in the unprotected cycloadduct.

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Scheme 3: Attempts for hydrolysis of the enol phosphate under basic conditions.

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Scheme 4: Cleavage of enol phosphate with Red-Al.

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Scheme 5: Synthesis of the protected central fragment 11b.

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Scheme 6: Synthesis and derivatization of the lactone fragment.

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Scheme 7: Coupling reaction between alkyne 19 and ketone 11b.

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Scheme 8: Coupling reaction between vinyl iodide 20 and ketone 11b.

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Scheme 9: Oxidation of the acetal to the lactone.

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Album

Full Research Paper

Published 04 Oct 2022

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