Studies toward the Synthesis of an Oxazole-Based Analog of (-)-Zampanolide.
Christian P BoldCindy KlausBernhard PfeifferJasmine SchürmannRafael LombardiDaniel Lucena-AgellJosé Fernando DíazKarl-Heinz AltmannPublished in: Organic letters (2021)
Studies are described toward the synthesis of an oxazole-based analog of (-)-zampanolide (2). Construction of (-)-dactylolide analog 22 was achieved via alcohol 5 and acid 4 through esterification and Horner-Wadsworth-Emmons (HWE)-based macrocyclization; however, attempts to attach (Z,E)-sorbamide to 22 proved unsuccessful. The C(8)-C(9) double bond of the macrocycle was prone to migration into conjugation with the oxazole ring, which may generally limit the usefulness of zampanolide analogs with aromatic moieties as tetrahydropyran replacements.
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