Mukaiyama and Torgov Chemistry in the Synthesis of (D-homo) Steroid Skeletons

Saraber, F.; Drach, S.; Baranovsky, A.; Charnikhova, T.; Pogrebnoi, S.; Jansen, B.; Groot, A.

Artykuł - szczegóły

Tytuł artykułu

Mukaiyama and Torgov Chemistry in the Synthesis of (D-homo) Steroid Skeletons

Autorzy

Saraber F. , Drach S. , Baranovsky A. , Charnikhova T. , Pogrebnoi S. , Jansen B. , Groot A.

Identyfikatory

Warianty tytułu

Konferencja

21st Conference on Isoprenoids, 23-29 September 2005, Białystok-Białowieża, Poland

Języki publikacji

Abstrakty

Three new, short, and efficient procedures have been developed for syntheses of steroid and D-homo steroid skeletons by application of Mukaiyama and Torgov chemistry. An important element in the first and in the second route is a Mukaiyama-Michael reaction with transfer of the silyl group from the starting silyl enol ether to the carbonyl group of the receiving enone. In this way a new silyl enol ether is obtained which enables either a selective reaction with the silyl enol ether in ring D as in route 1, or a selective reaction with the unprotected carbonyl group in ring B as in route 2. In all three approaches the C12-C13 bond is constructed using a Mukaiyama reaction of a Torgov type carbocation precursor with a silyl enol ether as the key transformation. In route 1, Zieglers triketone, which has been used before in the synthesis of 9,11-dehydroestrone methyl ether, has been prepared in four easy steps and in 70% overall yield, using the reactions mentioned above. In the second route a selective Grignard reaction of vinyl magnesium bromide with the unprotected carbonyl group of methoxy tetralone leads to a Torgov type intermediate. This can be converted easily into a carbocation, which then reacts intramolecularly with the silyl enol ether in ring D, under formation of the C12-C13 bond to complete the synthesis of cis (D-homo) steroid skeletons. In the third route, C17 substituted C,Dtrans coupled (D-homo) steroid skeletons have been prepared via an intermolecular addition of a carbocation, generated with ZnBr2 from a Torgov reagent, to a silyl enol ether containing ring D precursor. The adducts have been cyclized under formation of the C8-C14 bond by treatment with acid and the double bonds in the cyclized products have been reduced to all trans steroid skeletons. A chiral five membered silyl enol ether containing ring D precursor has been synthesized from carvone, and used as starting compound in the synthesis of a chiral C17 functionalized steroid.

Słowa kluczowe

Torgov reagent Mukaiyama-Michael addition silyl enol ethers (D-homo) steroid synthesis carvone

Wydawca

Polskie Towarzystwo Chemiczne

Czasopismo

Polish Journal of Chemistry

Rocznik

2006

Tom

Vol. 80, nr 4

Strony

535--548

Opis fizyczny

Bibliogr. 64 poz.

Twórcy

autor

Saraber F.

autor

Drach S.

autor

Baranovsky A.

autor

Charnikhova T.

autor

Pogrebnoi S.

autor

Jansen B.

autor

Groot A.

Laboratory of Organic Chemistry, Wageningen University, Dreijenplein 8, 6703 HB Wageningen, The Netherlands

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Typ dokumentu

Bibliografia

Identyfikator YADDA

bwmeta1.element.baztech-article-BUJ3-0006-0052