Synthetic studies of the 18-membered antitumor macrolide, tedanolide. 3. Stereocontrolled synthesis of the C1-C12 part via a synthesis of the C1-C7 fragment by a mismatched but efficient sharpless dihydroxylation and its coupling with the C8-C11 fragment.

The C1-C12 part (4) of tedanolide (1) was synthesized starting from methyl (R)-3-hydroxy-2-methylpropionate (11a) via a coupling between the C1-C7 aldehyde (6) and the C8-C11 iodoalkene (7a). For a synthesis of 6, a mismatched but highly efficient Sharpless dihydroxylation of the alpha, beta-unsaturated ester (15) with AD-mix-alpha was successfully applied. Compound 7a was synthesized using hydrozirconation to the alkyne (32).

泰得内酯（1）的C1 - C12部分（4）是从（R）-3-羟基-2-甲基丙酸甲酯（11a）出发，通过C1 - C7醛（6）和C8 - C11碘代烯烃（7a）之间的偶联反应合成的。对于6的合成，成功应用了用AD - mix -α对α，β -不饱和酯（15）进行的不匹配但高效的夏普莱斯双羟基化反应。化合物7a是通过对炔烃（32）进行氢锆化反应合成的。