期刊
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
卷 2013, 期 30, 页码 6789-6792出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/ejoc.201301065
关键词
Asymmetric synthesis; Olefination; Oxidation; Rearrangement; Amino acids
资金
- Ministry of Education, Culture, Sports, Science and Technology (MEXT) of Japan [12045232]
- Uehara Memorial Foundation
- Grants-in-Aid for Scientific Research [23390007, 24105530, 24102525, 12045232] Funding Source: KAKEN
We describe herein the asymmetric total synthesis of sphingofungin E, which has potent immunosuppressive activity. Key steps include asymmetric desymmetrization by bromolactonization, stereocontrolled construction of four contiguous stereogenic centers through allylic C-H oxidation and epoxide ring opening, regioselective elongation of a dialdehyde, and Hofmann rearrangement by using PhI(OCOCF3)(2).
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