A new approach toward the synthesis of C,D-cis coupled steroid and C,D-cis coupled d-homosteroid skeletons

Dratch, Svetlana; Charnikhova, Tanya; Sarabèr, Florence C.E.; Jansen, B. J. M.; Groot, Aede de

doi:10.1016/s0040-4020(03)00629-x

Cited by 12 publications

(3 citation statements)

References 20 publications

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“…22 The requisite TBS silyl enol ether 20 was rst synthesized through treatment of enantioenriched chromanone 3 with triethylamine, TBSCl and NaI. 41 The resulting TBS ether (20) was then exposed to Cu(OTf) 2 /Cu 2 O in the presence of 2,6-di-t-butylpyridine (DTBP). These oxidative conditions directly yielded the natural product (À)-deguelin in 25% yield, with the remainder of the mass balance identied as over-oxidized decomposition products.…”

Section: Resultsmentioning

confidence: 99%

A concise enantioselective synthesis and cytotoxic evaluation of the anticancer rotenoid deguelin enabled by a tandem Knoevenagel/conjugate addition/decarboxylation sequence

Farmer

Scheidt

2013

Chem. Sci.

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(−)-Deguelin is a rotenoid natural product that possesses significant potential as a chemopreventive and chemotherapeutic agent. While several racemic syntheses of deguelin have been reported, a formal evaluation of the anticancer activity of both the natural and unnatural enantiomers remains lacking. We describe herein the successful application of a flexible and selective thiourea-catalyzed cyclization strategy toward the enantioselective total synthesis of deguelin, which allows access to either stereoisomer for biological studies. The synthesis was completed in six steps (longest linear) with no protecting groups. The evaluation of both enantiomers of the natural product demonstrated potent inhibition of several cancer cell lines by these compounds, but interestingly showed that the unnatural (+)-deguelin preferentially inhibited the growth of MCF-7 breast cancer and HepG2 liver carcinoma cells when compared to the natural product.

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Section: Resultsmentioning

confidence: 99%

A concise enantioselective synthesis and cytotoxic evaluation of the anticancer rotenoid deguelin enabled by a tandem Knoevenagel/conjugate addition/decarboxylation sequence

Farmer

Scheidt

2013

Chem. Sci.

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“…overall yields of about 50% can be achieved in four steps in this way (Scheme 15). 52,53 On the basis of Mukaiyama chemistry, a further efficient procedure has been developed to obtain C,Dcis annelated D-homosteroids. 54…”

Section: Scheme 14mentioning

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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“…The synthesis of functionalized steroid skeletons in overall yields of about 50% can be achieved in four steps in this way (Scheme 15). 52,53 On the basis of Mukaiyama chemistry, a further efficient procedure has been developed to obtain C,Dcis annelated D-homosteroids. …”

Section: Scheme 14mentioning

confidence: 99%

Recent Developments in the Isolation and Synthesis of D‐Homosteroids and Related Compounds

Wölfling¹

2007

ChemInform

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A new approach toward the synthesis of C,D-cis coupled steroid and C,D-cis coupled d-homosteroid skeletons

Cited by 12 publications

References 20 publications

A concise enantioselective synthesis and cytotoxic evaluation of the anticancer rotenoid deguelin enabled by a tandem Knoevenagel/conjugate addition/decarboxylation sequence

A concise enantioselective synthesis and cytotoxic evaluation of the anticancer rotenoid deguelin enabled by a tandem Knoevenagel/conjugate addition/decarboxylation sequence

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

Recent Developments in the Isolation and Synthesis of D‐Homosteroids and Related Compounds

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