Total synthesis of hemibrevetoxin B via the allylic tin methodology

Isao Kadota; Yoshinori Yamamoto

doi:10.1515/MGMC.1996.19.6.361

Total synthesis of hemibrevetoxin B via the allylic tin methodology

Isao Kadota, Yoshinori Yamamoto

Research output: Contribution to journal › Article › peer-review

6 Citations (Scopus)

Abstract

The total synthesis of Hemibrevetoxin B is described. A new cyclization approach, based on the Lewis acid mediated intramolecular cyclization of the γ-oxo-substituted allylic tin having an aldehyde group, produced the 6-6-7-7 polycyclic ether skeleton of the natural product with high stereoselectivity. The ¹H and ¹³C-NMR spectra of synthetic hemibrevetoxin B was identical with those of natural product.

Original language	English
Pages (from-to)	361-366
Number of pages	6
Journal	Main Group Metal Chemistry
Volume	19
Issue number	6
DOIs	https://doi.org/10.1515/MGMC.1996.19.6.361
Publication status	Published - Jan 1 1996
Externally published	Yes

ASJC Scopus subject areas

Chemistry(all)
Condensed Matter Physics
Metals and Alloys
Materials Chemistry

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abstract = "The total synthesis of Hemibrevetoxin B is described. A new cyclization approach, based on the Lewis acid mediated intramolecular cyclization of the γ-oxo-substituted allylic tin having an aldehyde group, produced the 6-6-7-7 polycyclic ether skeleton of the natural product with high stereoselectivity. The 1H and 13C-NMR spectra of synthetic hemibrevetoxin B was identical with those of natural product.",

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AB - The total synthesis of Hemibrevetoxin B is described. A new cyclization approach, based on the Lewis acid mediated intramolecular cyclization of the γ-oxo-substituted allylic tin having an aldehyde group, produced the 6-6-7-7 polycyclic ether skeleton of the natural product with high stereoselectivity. The 1H and 13C-NMR spectra of synthetic hemibrevetoxin B was identical with those of natural product.

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Total synthesis of hemibrevetoxin B via the allylic tin methodology

Abstract

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