Selective reactions and modification of functional groups in steroid chemistry

https://aasldpubs.onlinelibrary.wiley.com/doi/pdf/10.1002/hep.1840070210

Accumulation of 7α-hydroxy-4-cholesten-3-one and cholesta-4,6-dien-3-one in patients with cerebrotendinous xanthomatosis: Effect of treatment with chenodeoxycholic acid

A mild and efficient selective tetrahydropyranylation of primary alcohols and deprotection of THP ethers of phenols and alcohols using PdCl2(CH3CN)2 as catalyst

Ceric Ammonium Nitrate Catalysed Protection of Alcohols by 3, 4-Dihydro-2H-pyran

Acid-catalysed addition of isobutene to steroidal alcohols gives the t-butyl ethers in high yields. These ethers are acid-labile, but alkali-resistant.

The t-butyl group is readily split off with trifluoroacetic acid.

The usefulness of the method is demonstrated by a simple synthesis of testosterone benzoate from dehydroepiandrosterone.

H. B. Henbest

Papers

445. Studies in the sterol group. Part LIII. The preparation of 7-hydroxy-3-keto-Δ4-steroids

266. Studies in the sterol group. Part LI. Reactions between 17-keto-steroids and organometallic compounds