The Preparation of the Spirostanic Analogues of Brassinolide and Castasterone

• Autorzy: Rodríguez C. , Zullo M. , Queiróz H. , Azevedo de M. , Becerra E. , Manchado F.
• Konferencja: 21st Conference on Isoprenoids, 23-29 September 2005, Białystok-Białowieża, Poland
• Języki publikacji: EN

Abstrakty

EN

Methods for the preparation of the spirostanic analogues of brassinosteroids (25R)-5alfa- spirostan-6-one-2alfa,3alfa-diol and (25R)-B-homo-5alfa-spirostan-6-oxo-7-oxalactone- 2alfa,3alfa-diol, starting from diosgenin, were examined. The best preparative route was via diosgenin tosylation, isosteroidal rearrangement with potassium acetate in aqueous acetone, oxidation with Jones reagent, cyclopropyl ring opening with hydrobromic acid, hydrogen bromide elimination with lithium bromide and carbonate, dihydroxylation with osmium tetroxide and N-methylmorpholine N-oxide, producing (25R)-5alfa- spirostan-6-one-2alfa,3alfa-diol in 57.3% overall yield and lactonization with trifluoroperoxyacetic acid producing (25R)-B-homo-5alfa-spirostan-6-oxo-7-oxalactone- 2alfa,3alfa-diol in 24.6% overall yield from diosgenin. The shortest route to (25R)-5alfa-spirostan-6-one-2alfa,3alfa-diol results in only 39.4% overall yield.

Słowa kluczowe

EN

brassinosteroids; spirostanic analogues

• Wydawca: Polskie Towarzystwo Chemiczne
• Czasopismo: Polish Journal of Chemistry
• Rocznik: 2006
• Tom: Vol. 80, nr 4
• Strony: 637--646
• Opis fizyczny: Bibliogr. 27 poz.

Twórcy

autor

Rodríguez C.

autor

Zullo M.

autor

Queiróz H.

autor

Azevedo de M.

autor

Becerra E.

autor

Manchado F.

• Laboratorio de Productos Naturales, Facultad de Química, Universidad de La Habana, Calzada de Zapata y Calle G, Vedado, Habana 10400, Cuba

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