Total synthesis and structural revision of sekothrixide.
The first total synthesis of 14-membered macrolide sekothrixide and the originally proposed structure are reported. Seven contiguous asymmetric centers in the side chain were constructed using ring-openings of several kinds of epoxide. Assembly of the left segment and right segment was performed on the basis of the RCM reaction to generate 14-membered lactones having an E-trisubstituted olefin. These synthetic results led to a revision of C4, C6, and C8 stereochemistry in the structure of natural sekothrixide.
Department of Applied Chemistry Kogakuin University Nakano 2665-1, Hachioji, Tokyo 192-0015, Japan.
Naoki
N
Terayama
Eiko
E
Yasui
Megumi
M
Mizukami
Masaaki
M
Miyashita
Shinji
S
Nagumo
D006571:Heterocyclic Compounds / Q000138:chemical synthesis / Q000737:chemistry; D007783:Lactones / Q000737:chemistry*; D018942:Macrolides / Q000138:chemical synthesis* / Q000737:chemistry*; D015394:Molecular Structure; D013237:Stereoisomerism
D006571:Heterocyclic Compounds; D007783:Lactones; D018942:Macrolides; C072162:sekothrixide