Convergent syntheses of the WXYZ ring of maitotoxin and the HIJK ring of brevisulcenal-F

Naoya Osato, Hisaaki Onoue, Yoshiki Toma, Kohei Torikai, Makoto Ebine, Masayuki Satake, Tohru Oishi

Research output: Contribution to journalArticle

4 Citations (Scopus)

Abstract

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.

Original languageEnglish
Pages (from-to)265-268
Number of pages4
JournalChemistry Letters
Volume47
Issue number3
DOIs
Publication statusPublished - Jan 1 2018

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Ketones
Stereochemistry
Methylation
Lithium
Aldehydes
Ether
maitotoxin
brevisulcenal-F

All Science Journal Classification (ASJC) codes

  • Chemistry(all)

Cite this

Convergent syntheses of the WXYZ ring of maitotoxin and the HIJK ring of brevisulcenal-F. / Osato, Naoya; Onoue, Hisaaki; Toma, Yoshiki; Torikai, Kohei; Ebine, Makoto; Satake, Masayuki; Oishi, Tohru.

In: Chemistry Letters, Vol. 47, No. 3, 01.01.2018, p. 265-268.

Research output: Contribution to journalArticle

Osato, Naoya ; Onoue, Hisaaki ; Toma, Yoshiki ; Torikai, Kohei ; Ebine, Makoto ; Satake, Masayuki ; Oishi, Tohru. / Convergent syntheses of the WXYZ ring of maitotoxin and the HIJK ring of brevisulcenal-F. In: Chemistry Letters. 2018 ; Vol. 47, No. 3. pp. 265-268.
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