| 초록 |
(-)-Zampanolide having a unsaturated 20 membered macrolactone incorporating a cis-2,6-disubstituted tetrahydropyran exhibit significant cytotoxic activity(IC50 1-5 ng/mL) against a variety of tumor cell lines including P388, HT29, A549, and MEL28. The impressive biological activity and unique structure attract great attention. For the synthesis of (-)-Zampanolide, here in We describe the new efficient synthetic approach toward cis-2,6-disubstituted tetrahydropyran unit by stereo selective intramolecular addition of a cyclopropanol moiety to highly functionalized aldehyde fragment. The cyclopropanol moiety synthesized via Ti mediated hydroxylcyclopropanation of homoallylic alcohol in which 1,4-diol arrayed on the oxocarbenium ion prepared form proper aldehyde under the condition suggested by Noyori group prompting 7-membered acetal intermediate, and this intermediate might rearrange to the cis-2,6-disubstituted tetrahydropyran unit.
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