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1 article(s) from Schuster, Hannah

Synthesis of the B-seco limonoid core scaffold

Hanna Bruss,
Hannah Schuster,
Rémi Martinez,
Markus Kaiser,
Andrey P. Antonchick and
Herbert Waldmann

Beilstein J. Org. Chem. 2014, 10, 194–208, doi:10.3762/bjoc.10.15

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Graphical Abstract

Figure 1: Structures of the 4,4,8-trimethyl-17-furanylsteroid core structure I and the representative B-seco ...

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Scheme 1: Retrosynthetic analysis of the B-seco limonoid framework employing a [3,3]-sigmatropic rearrangemen...

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Scheme 2: Retrosynthetic analysis of the B-seco limonoid scaffold employing a Claisen rearrangement as key st...

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Scheme 3: Synthesis of alcohols 19, 20 and 22. Reagents and conditions: a) CSA, 2,3-butanedione, trimethyl or...

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Scheme 4: Retrosynthetic analysis of the B-seco limonoid scaffold employing an Ireland–Claisen rearrangement ...

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Scheme 5: Synthesis and Ireland–Claisen rearrangement of the allyl esters 27, 28, 29 and 30. Reagents and con...

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Figure 2: Conformation of rearrangement precursor 30 and possible transition state involved in the Ireland–Cl...

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Scheme 6: Synthesis of model C rings 40, 41 and 42. Reagents and conditions: a) TBDPSCl, DMAP, NEt₃, CH₂Cl₂, ...

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Scheme 7: β-Substituted allyl esters tested in the Ireland–Claisen and the Carroll rearrangement.

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Scheme 8: Synthesis and Ireland–Claisen rearrangement of bicyclic allyl ester precursor 66. Reagents and cond...

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Figure 3: Conformations of rearrangement precursors 66 and 77 and possible transition states involved in the ...

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Scheme 9: Synthesis and Ireland–Claisen rearrangement of allyl ester 70. Reagents and conditions: a) DIPEA, M...

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Scheme 10: Synthesis and Ireland–Claisen rearrangement of allyl ester 72. Reagents and conditions: a) TIPSOTf,...

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Scheme 11: Synthesis of the C14-epi and C14/C9-epi B-seco limonoid scaffolds 78 and 79. Reagents and condition...

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Scheme 12: Synthesis of fully functionalized A ring 87. Reagents and conditions: a) HO(CH₂)₂OH, THF, Pd/C, H₂,...

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Scheme 13: and Attempted Ireland–Claisen rearrangement of allyl ester 88. R¹ = MOM, R² = CO₂H.

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Scheme 14: Synthesis and attempted Ireland–Claisen rearrangement of allyl ester 93. Reagents and conditions: a...

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Scheme 15: Allyl esters tested in the Ireland–Claisen rearrangement.

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Published 16 Jan 2014

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