5869-16-9Relevant academic research and scientific papers
Stereospecific cis-Reduction of Hexahydro-3-oxophenanthrene Derivatives. Total Synthesis of a New Class of Ring-c Aromatic Steroid
Chatterjee, Amareshwar,Chaudhuri, Swadesh R. Ray,Chatterjee, Swapan K.
, p. 24 - 25 (1982)
Catalytic hydrogenation (Pd/C, 10percent) of the hexahydro-3-oxophenanthrene (2a) in acidic medium gave the trans-fused octahydrophenanthrene ring system (5b) predominantly, whereas reduction of (2a-c) with LiAlH4 followed by oxidation gave exclusively the cis-fused systems (4a), (4c), and (4e), respectively; the products (4a) and (5b) have been elaborated to the 10βH and 10αH isomers, respectively, of 5,12-dimethyl-5β-gonane-8,11,13-triene-17-one.
Stereoselectivity and Stereospecificity in Reductions of Some Hexahydro-3-oxophenanthrene Derivatives with Various Reducing Agents
Chatterjee, S. K.,Bhattacharya, S.,Raychaudhuri, S.R.,Chatterjee, A.
, p. 1191 - 1199 (2007/10/02)
Catalytic and chemical reduction of hexahydro-3-oxophenanthrene derivatives (1a,b) and (1d,e) are reported.Catalytic hydrogenation (Pd/C,10percent) of 1a and 1b in acidic medium affords predominantly the trans-fused hydrocarbons (2a) and (2c) respectively, whereas similar hydrogenation of 1a in pyridine solution gives the cis-fused ketone (3b) as the major product.Birch reduction of 1a and 1b affords in each case a 65:35 mixture of the corresponding saturated cis- and trans-fused ketones.Reduction of 1a and 1b with Ni-Al alloy and alkali followed by oxidation furnish selectively the trans-fused ketones (3a) and (3c).Lithium aluminium hydride reduction of 1a,b and 1d,e followed by oxidation provided exclusively the cis-fused ketones (3b),(3d),(3f), and (3h) respectively.The stereospecificity observed in LAH reduction, and the lower yields of the reduction products in the case of 1b and 1e, have been rationalised.
