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Beilstein J. Org. Chem. 2014, 10, 194–208, doi:10.3762/bjoc.10.15
Graphical Abstract
Figure 1: Structures of the 4,4,8-trimethyl-17-furanylsteroid core structure I and the representative B-seco ...
Scheme 1: Retrosynthetic analysis of the B-seco limonoid framework employing a [3,3]-sigmatropic rearrangemen...
Scheme 2: Retrosynthetic analysis of the B-seco limonoid scaffold employing a Claisen rearrangement as key st...
Scheme 3: Synthesis of alcohols 19, 20 and 22. Reagents and conditions: a) CSA, 2,3-butanedione, trimethyl or...
Scheme 4: Retrosynthetic analysis of the B-seco limonoid scaffold employing an Ireland–Claisen rearrangement ...
Scheme 5: Synthesis and Ireland–Claisen rearrangement of the allyl esters 27, 28, 29 and 30. Reagents and con...
Figure 2: Conformation of rearrangement precursor 30 and possible transition state involved in the Ireland–Cl...
Scheme 6: Synthesis of model C rings 40, 41 and 42. Reagents and conditions: a) TBDPSCl, DMAP, NEt3, CH2Cl2, ...
Scheme 7: β-Substituted allyl esters tested in the Ireland–Claisen and the Carroll rearrangement.
Scheme 8: Synthesis and Ireland–Claisen rearrangement of bicyclic allyl ester precursor 66. Reagents and cond...
Figure 3: Conformations of rearrangement precursors 66 and 77 and possible transition states involved in the ...
Scheme 9: Synthesis and Ireland–Claisen rearrangement of allyl ester 70. Reagents and conditions: a) DIPEA, M...
Scheme 10: Synthesis and Ireland–Claisen rearrangement of allyl ester 72. Reagents and conditions: a) TIPSOTf,...
Scheme 11: Synthesis of the C14-epi and C14/C9-epi B-seco limonoid scaffolds 78 and 79. Reagents and condition...
Scheme 12: Synthesis of fully functionalized A ring 87. Reagents and conditions: a) HO(CH2)2OH, THF, Pd/C, H2,...
Scheme 13: and Attempted Ireland–Claisen rearrangement of allyl ester 88. R1 = MOM, R2 = CO2H.
Scheme 14: Synthesis and attempted Ireland–Claisen rearrangement of allyl ester 93. Reagents and conditions: a...
Scheme 15: Allyl esters tested in the Ireland–Claisen rearrangement.