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Stereocontrolled Total Synthesis of Sphingofungin E
Author(s) -
Ikeuchi Kazutada,
Hayashi Moemi,
Yamamoto Tomohiro,
Inai Makoto,
Asakawa Tomohiro,
Hamashima Yoshitaka,
Kan Toshiyuki
Publication year - 2013
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201301065
Subject(s) - desymmetrization , stereocenter , chemistry , regioselectivity , stereochemistry , epoxide , allylic rearrangement , total synthesis , ring (chemistry) , enantioselective synthesis , organic chemistry , catalysis
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(OCOCF 3 ) 2 .