Enantioselective total synthesis of convolutamydines B and E.
[reaction: see text] The first enantioselective total synthesis of convolutamydines B and E has been achieved using our vinylogous Mukaiyama aldol reaction. The synthesis features highly diastereoselective vinylogous Mukaiyama aldol reaction with isatin instead of aldehydes to construct a chiral center of convolutamydines. Additionally, the absolute configuration of natural convolutamydine B has been determined as R by its CD spectrum.
Nakamura
Tomoaki
T
Faculty of Pharmaceutical Sciences, Tokyo University of Science (RIKADAI), 2641 Yamazaki, Noda-shi, Chiba, 278-8510, Japan.
Shirokawa
Shin-ichi
S
Hosokawa
Seijiro
S
Nakazaki
Atsuo
A
Kobayashi
Susumu
S
D000818:Animals; D002013:Bryozoa / Q000737:chemistry; D002384:Catalysis; D002942:Circular Dichroism; D026121:Indole Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry; D007510:Isatin / Q000031:analogs & derivatives* / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure
D026121:Indole Alkaloids; C514308:convolutamydine B; C514307:convolutamydine E; D007510:Isatin