Tetrahedron Letters p. 2833 - 2836 (1994)
Update date:2022-08-24
Topics:
Kym, Philip R.
Wilson, Scott R.
Gritton, William H.
Katzenellenbogen, John A.
Cetyltrimethylammonium permanganate initiates oxidative opening of the D-ring of 16-dehydroprogesterone in CH2Cl2. The novel steroids 3 and 4 have been isolated and characterized as the major products obtained from oxidative rearrangement of the steroid backbone. The X-ray crystal structure of the D-homosteroid 3 is provided, and a putative mechanism that invokes a benzilic acid rearrangement for formation of 3 is presented.
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