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Iodolactonization of derivatives of 30-hydroxypregna-5,20-dien-17 -acetic acid (7) afforded the corresponding 2 l-iodo-20/3-hydroxy lactones (8a, 9a, and 9b). Displacement of the iodide by various nucleophiles afforded the corresponding 21-substituted analogs (8b, 8c, 8f, 9d-h, and 12), and catalytic reduction yielded the 21-unsubstituted compounds (8d, 8e, and 9c). Other spiro systems were prepared from 35-hydroxy-5ct-pregn-20-en-l7cracetic acid (7b) by ozonolysis followed by reduction (18) and oxidation (19).

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