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1 article(s) from Schleicher, Kristin D

A reductive coupling strategy towards ripostatin A

Kristin D. Schleicher and
Timothy F. Jamison

Beilstein J. Org. Chem. 2013, 9, 1533–1550, doi:10.3762/bjoc.9.175

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Graphical Abstract

Figure 1: Structures of the ripostatins.

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Figure 2: Retrosynthesis of ripostatin A.

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Scheme 1: Nickel-catalyzed reductive coupling of alkynes and epoxides.

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Figure 3: Proposed retrosynthesis of ripostatin A featuring enyne–epoxide reductive coupling and rearrangemen...

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Scheme 2: Potential transition states and stereochemical outcomes for a concerted 1,5-hydrogen rearrangement.

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Scheme 3: Rearrangements of vinylcyclopropanes to acylic 1,4-dienes.

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Scheme 4: Synthesis of cyclopropyl enyne.

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Scheme 5: Synthesis of model epoxide for investigation of the nickel-catalyzed coupling reaction.

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Scheme 6: Nickel-catalyzed enyne–epoxide reductive coupling reaction.

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Scheme 7: Proposed mechanism for the nickel-catalyzed coupling reaction of alkynes or enynes with epoxides.

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Scheme 8: Regioselectivity changes in reductive couplings of alkynes and 3-oxygenated epoxides.

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Scheme 9: Enyne reductive coupling with 1,2-epoxyoctane.

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Figure 4: Initial retrosynthesis of the epoxide fragment by using dithiane coupling.

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Scheme 10: Synthesis of dithiane by Claisen rearrangement.

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Scheme 11: Deuterium labeling reveals that the allylic/benzylic site is most acidic.

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Scheme 12: Oxy-Michael addition to δ-hydroxy-α,β-enones.

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Figure 5: Revised retrosynthesis of epoxide 5.

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Scheme 13: Synthesis of functionalized ketone by oxy-Michael addition.

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Figure 6: Retrosynthesis by using iodocylization to introduce the epoxide.

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Scheme 14: Synthesis of ketone 57 using thiazolidinethione chiral auxiliary.

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Figure 7: Retrosynthesis involving decarboxylation of a β-ketoester.

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Scheme 15: Synthesis of β-ketoester 61.

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Scheme 16: Decarboxylation of 61 under Krapcho conditions.

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Scheme 17: Improved synthesis of 63 and attempted iodocyclization.

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Figure 8: Retrosynthesis utilizing Rychnovsky’s cyanohydrin acetonide methodology.

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Scheme 18: Synthesis of cyanohydrin acetonide and attempted alkylation with epoxide.

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Scheme 19: Allylation of acetonide and conversion to aldehyde.

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Scheme 20: Synthesis of the epoxide precursor by an aldol−decarboxylation sequence.

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Published 31 Jul 2013

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