Athanasiadou Theodora, Bagkavou Georgia G, Karagianni Polymnia, Stathakis Christos I
Department of Chemistry, Aristotle University of Thessaloniki, Thessaloniki 541 24, Greece.
Org Lett. 2024 Apr 19;26(15):2897-2901. doi: 10.1021/acs.orglett.4c00132. Epub 2024 Mar 29.
Terpenes represent a flourishing source of structural motifs that can be converted into several more complex architectures. Realization of such transformations in a concise and efficient manner adds great value to the starting material. Herein, we study the case of (-)-caryophyllene oxide and convert it into natural sesquiterpenoids (rumphellolide K, rumphellaone A, and antipacid A), thus expanding the chemical space accessed by its privilege structure. Our semisyntheses are short and rely on reagent-dictated stereo- and chemoselectivity.
萜类化合物是丰富的结构基序来源，可转化为多种更复杂的结构。以简洁高效的方式实现此类转化会为起始原料增添巨大价值。在此，我们研究了（-）-石竹烯氧化物的情况，并将其转化为天然倍半萜类化合物（rumphellolide K、rumphellaone A和抗酸剂A），从而扩展了其优势结构所能涉及的化学空间。我们的半合成路线简短，且依赖于试剂导向的立体和化学选择性。
