Total synthesis of (±)-5β,8α- androst-9(11)-ene-3,17-dione
1979 ◽
Vol 57
(24)
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pp. 3354-3356
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A total synthesis of (±)-5β,8α- androst-9(11)-ene-3,17-dione is described. The key step is a ring C forming SnCl4-catalyzed Diels–Alder reaction in which the geometry of the diene controls syn–anti stereochemistry while the catalyst guides the addition to the desired endo orientation. A preparation of ethyl E-2-methyl-4-oxo-2-butenoate and the dehydration of a tertiary allylic alcohol by the pyrolysis of the corresponding tosyl carbamate are also described.
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1999 ◽
Vol 40
(14)
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pp. 2769-2772
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1980 ◽
Vol 102
(22)
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pp. 6893-6894
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1985 ◽
Vol 50
(20)
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pp. 3738-3749
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Keyword(s):
2010 ◽
Vol 51
(39)
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pp. 5116-5119
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