Convergent Syntheses of the WXYZ Ring of Maitotoxin and the HIJK Ring of Brevisulcenal-F

作者:Osato Naoya; Onoue Hisaaki; Toma Yoshiki; Torikai Kohei; Ebine Makoto; Satake Masayuki; Oishi Tohru*
来源:Chemistry Letters, 2018, 47(3): 265-268.
DOI:10.1246/cl.171056

摘要

A convergent method to construct the 6/7/6/6-tetracyclic ether system possessing contiguous angular methyl groups was developed. The key steps of the synthesis involve coupling of a lithium acetylide and an aldehyde, cyclodehydration of a hydroxy ketone to form a dihydropyran, ring expansion of a six-membered ring ketone into a seven-membered one, and methylation of a mixed-thioacetal. Based on this strategy, syntheses of the WXYZ ring of maitotoxin and the HIJK ring of brevisulcenal-F were achieved, and the stereochemistry of the HIJK ring of brevisulcenal-F was confirmed.

  • 出版日期2018-3