663-39-8Relevant articles and documents
Metabolic fate of 3α,5-cycloandrostanes in the endogenous lactonization pathway of Aspergillus tamarii KITA
Hunter, A. Christy,Patel, Shreyal,Dedi, Cinzia,Dodd, Howard T.,Bryce, Richard A.
, p. 19 - 25 (2015)
A series of 3α,5-cycloandrostane analogues with a range of functionality (6α and 6β alcohols and ketone) at carbon 6 were tested in the endogenous lactonization pathway in Aspergillus tamarii KITA. This metabolic route converts progesterone to testololactone in high yield through a four step enzymatic pathway. To date, no studies have looked at the effect of steroids devoid of polar functionality at carbon 3 and their subsequent metabolic fate by fungi which contain Baeyer-Villiger monooxygenases. Incubation of all of the cycloandrostane analogues resulted in lactonization of ring-D irrespective of C-6 stereochemistry or absence of C-3 functionality. Presence of 6β-hydroxy group and the C-17 ketone was required in order for these analogues to undergo hydroxylation at C-15β position. All metabolites were isolated by column chromatography and were identified by 1H, 13C NMR, DEPT analysis and other spectroscopic data.
The Participation of 3,5-Cyclosteroids in Aromatization Reactions
Hanson, James R.,Knights, Steve G.
, p. 1306 - 1310 (2007/10/02)
The preparation of 6β,7β-dihydroxy-3α-5-cycloandrostan-17-one and 2β,17β-diacetoxy-6α-hydroxy-3α,5-cycloandrostane and their reaction with hydrobromic acid in acetic acid is described.They both afford the corresponding 4-methylestratriene accompanied by,