Total synthesis of Hemibrevetoxin B

Isao Kadota; Park Jung-Youl; Nagatoshi Koumura; Guy Pollaud; Yasuhisa Matsukawa; Yoshinori Yamamoto

doi:10.1016/00404-0399(50)10972-

Total synthesis of Hemibrevetoxin B

Isao Kadota, Park Jung-Youl, Nagatoshi Koumura, Guy Pollaud, Yasuhisa Matsukawa, Yoshinori Yamamoto

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

82 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)	5777-5780
Number of pages	4
Journal	Tetrahedron Letters
Volume	36
Issue number	32
DOIs	https://doi.org/10.1016/00404-0399(50)10972-
Publication status	Published - Aug 7 1995
Externally published	Yes

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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author = "Isao Kadota and Park Jung-Youl and Nagatoshi Koumura and Guy Pollaud and Yasuhisa Matsukawa and Yoshinori Yamamoto",

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AU - Kadota, Isao

AU - Jung-Youl, Park

AU - Koumura, Nagatoshi

AU - Pollaud, Guy

AU - Matsukawa, Yasuhisa

AU - Yamamoto, Yoshinori

PY - 1995/8/7

Y1 - 1995/8/7

N2 - 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.

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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JO - Tetrahedron Letters

JF - Tetrahedron Letters

SN - 0040-4039

IS - 32

ER -

Total synthesis of Hemibrevetoxin B

Abstract

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