Novel stereoids from cetyltrimethylammonium permanganate-initiated oxidative rearrangements of 16-dehydroprogesterone

DOI: 10.1016/S0040-4039(00)76637-8

Source and publish data:

Tetrahedron Letters p. 2833 - 2836 (1994)

Update date:2022-08-24

Topics:

Authors:

Kym, Philip R.

Wilson, Scott R.

Gritton, William H.

Katzenellenbogen, John A.

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Article abstract of DOI:10.1016/S0040-4039(00)76637-8

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.

Full text of DOI:10.1016/S0040-4039(00)76637-8

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