期刊
CHEMISTRY-A EUROPEAN JOURNAL
卷 17, 期 49, 页码 13754-13761出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201101437
关键词
cross-coupling; natural products; oxacycles; oxidation; polyethers
资金
- Ministry of Education, Culture, Sports, Science and Technology (MEXT), Japan [21651 090, 21 241 050]
- Japan Society for the Promotion of Sciences (JSPS)
- Grants-in-Aid for Scientific Research [23681045, 21241050, 23102016] Funding Source: KAKEN
We describe a streamlined strategy for the practical synthesis of trans-fused polycyclic ethers and its application to a concise total synthesis of (-)-brevenal, a new pentacyclic polyether natural product with intriguing biological activities. The B-, D-, and E-rings were constructed by TEMPO/PhI(OAc)2-mediated oxidative lactonization of the corresponding 1,6-diols, with minimal need for manipulation of oxygen functionalities. The B- and E-ring lactones were appropriately functionalized by SuzukiMiyaura coupling of lactone-derived enol phosphates and subsequent stereoselective hydroboration. The A-ring was formed by our mixed thioacetalization methodology. The AB- and DE-ring fragments were assembled through SuzukiMiyaura coupling, and the C-ring was forged in the same manner as that for the A-ring. More than two grams of the pentacyclic polyether core of (-)-brevenal have been synthesized by the synthetic route developed in this study.
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