ol5006856_si_001.pdf (12.92 MB)
Total Synthesis and Structural Revision of Sekothrixide
journal contribution
posted on 2014-06-06, 00:00 authored by Naoki Terayama, Eiko Yasui, Megumi Mizukami, Masaaki Miyashita, Shinji NagumoThe
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.