Chemically modified steroids have become increasingly important in medicine. Give the possible product(s) of the following reactions. In each case, identify the major stereoisomer formed on the basis of delivery of the attacking reagent from the less hindered side of the substrate molecule.
(a)

(b)

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OH CH, CH-CH 1. Excess CH,Mgl 2. H, H,O CH H HIH HO CH 3 I Excess CH,Li 2. H, HCo CHa H HIH