Studies in stereochemistry—I Stereospecific routes to trans- anti- and cis- syn-Δ-dodecahydrophenanthrenes |
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Authors: | S K Balasubramanian |
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Institution: | Department of Organic Chemistry, Indian Institute of Science, Bangalore India |
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Abstract: | Reduction of trans-1-oxo-7-methoxy-1,2,3,4,9,10,11,12-octahydrophenanthrene (XI) by lithium tri-t-butoxyaluminohydride gave trans-1β-hydroxy-7-methoxy-1,2,3,4,9,10,11,12-octahydrophenanthrene (XII) which on lithium—liquid ammonia reduction gave trans-anti-1β-hydroxy-7-oxo-Δ8(14)-dodecahydrophenanthrene (XIII). Reduction of cis-1-oxo-7-methoxy-1,2,3,4,9,10,11,12-octahydrophenanthrene (XV) by sodium borohydride gave cis-1 -hydroxy-7-methoxy-1,2,3,4,9,10,11,12-octahydrophenanthrene (XVI) which on lithium—liquid ammonia reduction gave cis-syn-1 -hydroxy-7-oxo-Δ8(14)-dodecahydrophenanthrene (XVII). |
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