Biomaterial Database

Short synthesis of 16beta-hydroxy-5alpha-cholestane-3,6-dione a novel cytotoxic marine oxysterol. 2006

Mickaël Denancé, and Michèle Guyot, and Mohammad Samadi

Département de Chimie, LIMBP, IPEM, Université Paul Verlaine de Metz, 1 Bd Arago, Metz Technopôle, 57078 Metz, France.

The first and short synthesis of 16beta-hydroxy-5alpha-cholestane-3,6-dione 1 a metabolite from marine algae, has been achieved in six steps from readily available diosgenin 5. Selective deoxygenation of primary alcohol of triol 6 has been accomplished in one step using Et(3)SiH and catalytic amount of B(C(6)F(5))(3) to produce compound 9 in high yield. Oxidation of 11 with PCC, allowed the introduction of 3,6-ene-dione functionality, and further catalytic hydrogenation and deprotection furnished the 3,6-diketo steroid 1.

UI	MeSH Term	Description	Entries
D008387	Marine Toxins	Toxic or poisonous substances elaborated by marine flora or fauna. They include also specific, characterized poisons or toxins for which there is no more specific heading, like those from poisonous FISHES.	Marine Biotoxins,Phycotoxins
D010084	Oxidation-Reduction	A chemical reaction in which an electron is transferred from one molecule to another. The electron-donating molecule is the reducing agent or reductant; the electron-accepting molecule is the oxidizing agent or oxidant. Reducing and oxidizing agents function as conjugate reductant-oxidant pairs or redox pairs (Lehninger, Principles of Biochemistry, 1982, p471).	Redox,Oxidation Reduction
D002384	Catalysis	The facilitation of a chemical reaction by material (catalyst) that is not consumed by the reaction.	Catalyses
D002778	Cholestanones	CHOLESTANES substituted with any number of keto groups.
D004144	Diosgenin	A spirostan found in DIOSCOREA and other plants. The 25S isomer is called yamogenin. Solasodine is a natural derivative formed by replacing the spiro-ring with a nitrogen, which can rearrange to SOLANINE.
D000461	Rhodophyta	Red algae whose color results from predominace of the red pigment (PHYCOERYTHRIN). However, if this pigment is destroyed, the algae can appear purple, brown, green, or yellow. Two important substances found in the cell walls of red algae are AGAR and CARRAGEENAN. Some rhodophyta are notable SEAWEED (macroalgae).	Algae, Red,Red Algae