As a team, consider the following schemes that outline steps toward the total synthesis of taxodone D, a potential anticancer agent. For the first scheme, divide your team into two groups, one to discuss the best option for A to effect the initial reduction step, the second to assign a structure to B, using the partial spectral data provided. 

Reconvene to discuss both parts of the first scheme. Then, as a group, analyze the remainder of the synthesis shown in the second scheme below. Use the spectroscopic data to help you determine the structures of C and taxodone, D.

Propose a mechanism for the formation of D from C.

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OCCH3 OCH3 CH;CO. CH;CO. H;C HẠC H*, toluene, A B 'H NMR: 8 = 5.99 (dd, 1 H), 6.50 (d, I H) ppm. IR: i = 1720 cm-. MS: mlz = 384 (M*). НО