A new flexible synthesis of (D-homo) steroids

Sarabèr, Florence C.E.; Groot, Aede de

doi:10.1016/j.tetlet.2004.10.102

Cited by 9 publications

(2 citation statements)

References 25 publications

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“…Having established the method for the construction of the [6.7.6.5]tetracyclic core structure 23 , we then shifted attention to investigating the formation of oxabicyclo[3.2.1]heptane core by directing the intramolecular Michael addition of the C-5 hydroxyl group to the Michael receptor in the presence of protic or Lewis acids. To this end, 23 was first subjected regioselective hydrogenation , to give 14 in 60% yield. The selectivity observed in this reaction might be attributed to the steric effect of the α-methyl group and also the high stability of the trans product.…”

Section: Resultsmentioning

confidence: 99%

Formal Synthesis of Cortistatins

et al. 2011

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Section: Resultsmentioning

confidence: 99%

Formal Synthesis of Cortistatins

et al. 2011

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“…50 A short, flexible, efficient method has been developed by Sarabèr and de Groot for the synthesis of 17-substituted steroid skeletons and D-homosteroid skeletons through the use of a ZnBr 2 -catalyzed coupling of a silyl enol ether-containing ring D precursor (53) with a Torgov-type reagent (52), followed by acidcatalyzed cyclization of the adducts (54), to furnish steroid and D-homosteroid skeletons (55; Scheme 14). 51…”

Section: Total Synthetic Approachesmentioning

confidence: 99%

Recent developments in the isolation and synthesis of D-homosteroids and related compounds

Wölfling

2007

Arkivoc

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Both naturally occurring and synthetic D-homologs of compounds with a sterane skeleton exhibit diverse biological activity. The main sources of isolation are plants and marine organisms. The synthetic D-homosteroids are potential leads for drug discovery. This review focuses on steroids with a six-membered carbocyclic ring D and related compounds, the isolation or syntheses of which were reported between the mid-1990s and mid-2006.

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