A ready synthesis of 5\u3b1,14\u3b2-cholest-7-en-3\u3b2-ol

Reduction of 3\u3b2-acetoxy-8\u3b1,14\u3b1-epoxy-5\u3b1-cholestan-7- one or 3\u3b2-acetoxy-5\u3b1-cholest-8(14)-en-7-one with zinc dust in methanolic N-sulphuric acid yields 3\u3b2-acetoxy-5\u3b1,14\u3b2-cholest-7- ene with minor amounts of 3\u3b2-acetoxy-5\u3b1,14\u3b2-cholestan-7-one, and constitutes a novel, simple synthesis of 14\u3b2-steroids

Side-chain inversion of steroidal olefins promoted by hydrogen chloride

The reaction of hydrogen chloride on 7-, 8(14)-, and 14-ene steroids was investigated. A 14\u3b1-chloro compound is the product of kinetically controlled addition of the acid. A 14\u3b2-chloro compound with the side chain in the 17\u3b1 configuration originates in diethyl ether at temperatures lower than -30\ub0C in the presence of hydrogen chloride, via a carbocation at C14. There is evidence that the inversion occurs through two distinct rearrangements involving the intermediary formation of a 12,14\u3b1-cyclo-12,13-seco-5\u3b1-cholest-13(17)-ene

Epoxidation of 7-double bond of cholesta-5,7-dien-3\u3b2-OL by permanganate

The 5,7-diene system of ring B unsaturated steroids is transformed by neutral or alkaline permanganate mainly into a 5\u3b1,6\u3b1-dihydroxy-7\u3b1,8\u3b1-epoxide and minor amounts of more polar compounds

A novel synthesis of 3\u3b2-hydroxy-5\u3b1-cholest-8(14)-en-15-one

Jones oxidation of 5\u3b1-cholesta-8,14-dien-3\u3b2-yl acetate furnishes 9\u3b1-hydroxy-15-oxo-5\u3b1-cholest-8(14)-en-3\u3b2-yl acetate (4a). Treatment of (4a) with zinc dust and sulphuric acid followed by saponification gives 3\u3b2-hydroxy-5\u3b1-cholest-8(14)-en-15-one. On the basis of chemical and spectroscopic evidence, the product obtained by oxidation of 5\u3b1-cholest-8,14-dien-3\u3b2-ol is formulated as 9\u3b1-hydroxy- 5\u3b1-cholest-8(14)-ene-3,15-dione (4b) and not as 14\u3b1-hydroxy- 5\u3b1-cholest-8-ene-3,7-dione (3) as reported by others

A simple method for the reduction of the 7,8-double bond of steroidal 5,7-dienes

1,4-Cycloadducts of various steroidal 5,7-dienes and 4-phenyl-1-2-4-triazoline-3,5-dione gave a separable mixture (3 : 2) of the corresponding \u3945- and \u3947-sterols in good yield when treated with lithium dissolved in refluxing rthylamine

Synthesis of (24R)- and (24S)-3\u3b2, 29-dihydroxystigmast-7-ene, a model for the side chain of oogoniol

(20S)-3\u3b2-Acetoxypregn-7-ene-20-carbaldehyde affords stereoselectively (24R)- and (24S)-3\u3b2,29-dihydroxystigmast-7-ene, compounds containing the side chain functionality of oogoniol, through a five step synthesis