Journal
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
Volume 2013, Issue 30, Pages 6789-6792Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/ejoc.201301065
Keywords
Asymmetric synthesis; Olefination; Oxidation; Rearrangement; Amino acids
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Funding
- 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
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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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