期刊
JOURNAL OF ORGANIC CHEMISTRY
卷 79, 期 15, 页码 6987-6995出版社
AMER CHEMICAL SOC
DOI: 10.1021/jo501142q
关键词
-
资金
- Hong Kong University of Science and Technology [HKUST R9309]
- Research Grant Council of Hong Kong [GRF ECS 605912, GRF 605113]
A new synthetic strategy was developed for the asymmetric total synthesis of (+)-didemniserinolipid B in 19 linear steps, featuring a highly efficient and enantioselective construction of 6,8-dioxabicyclo[3.2.1]octane (6,8-DOBCO) framework via a rarely explored Achmatowicz rearrangement/bicycloketalization strategy. In addition, the first total synthesis of the proposed (+)-didemniserinolipid C was accomplished with 41.6% yield in 4 steps from a common advanced intermediate 18, and a possible revised structure of (+)-didemniserinolipid C was proposed. The new convergent synthetic strategy greatly expedites the entry to the didemniserinolipids and their analogues for biological activity evaluation.
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