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Tetrahedron Letters
Volume 27, Issue 2, 1986, Pages 219-222

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doi:10.1016/S0040-4039(00)83981-7

A synthesis of novel nine-membered dienones through a cyclic acetylenic oxy-cope rearrangement: The synthesis of dl-phoracantholide I

Dedicated to Prof. Harry H. Wasserman on the occasion of his sixty-fifth birthday)

Takeshi Ohnuma, Noriaki Hata, Nobuhide Miyachi, Takeshi Wakamatsu and Yoshio Ban, ^*

Faculty of Pharmaceutical Sciences, Hokkaido University, Sapporo 060, Japan

Received 21 September 1985.

Available online 8 March 2001.

Abstract

Phoracantholide I, having a ten-membered lactone, was synthesized through a new synthetic method which includes a cyclic acetylenic oxy-Cope rearrangement and ring-expansion by the Baeyer-Villiger oxidation of a nine-membered ketone.

References

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Y. Fujita, T. Onishi, K. Hino and T. Nishida Tetrahedron Lett. 21 (1980), p. 1347. Abstract | PDF (183 K) | View Record in Scopus | Cited By in Scopus (3)

A.S. Gupta and S. Dev Tetrahedron 27 (1971), p. 635. Abstract | PDF (768 K) | View Record in Scopus | Cited By in Scopus (10)

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The following groups have synthesized 5 as an application of their own synthetic methodology. T. Wakamatsu, K. Akasaka and Y. Ban Tetrahedron Lett. 18 (1977), p. 2755. Abstract | PDF (171 K) | View Record in Scopus | Cited By in Scopus (3)
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T. Wakamatsu, S. Yamada, Y. Ozaki and Y. Ban Tetrahedron Lett. 26 (1985), p. 1989. Abstract | PDF (224 K) | View Record in Scopus | Cited By in Scopus (5)
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E. Vogel, W. Grimme and E. Dinne In: (Int. Ed. Engl. ed.),Ang. Chem. 2 (1963), p. 739. Full Text via CrossRef

T. Karihara, Y. Nakajima and O. Mitsunobu Tetrahedron Lett. (1976), p. 2455.

Ring-enlargement methods involving the cyclic acetylenic oxy-Cope reactions have recently been reported. Formation of eight-membered enone: R.C. Gadwood, R.M. Lett and J.E. Wissinger J. Am. Chem. Soc. 106 (1984), p. 3869. Full Text via CrossRef | View Record in Scopus | Cited By in Scopus (9)
R. Uma, S. Swaminathan and K. Rajagopalan Tetrahedron Lett. 25 (1984), p. 5825. Abstract | PDF (236 K) | View Record in Scopus | Cited By in Scopus (13)
N. Bluthe, M. Malacria and J. Gore Tetrahedron Lett. 25 (1984), p. 2873. Abstract | PDF (226 K) | View Record in Scopus | Cited By in Scopus (2)

The melting point(mp 122–4° C) of 2,4-dinitrophenylhydrazone derivative of our sample 16 was coincident with the following literature's (mp 123–4° C). E. Muller, M. Bauer and W. Rundel Tetrahedron Lett. (1961), p. 136. Abstract | PDF (168 K) | View Record in Scopus | Cited By in Scopus (0)
E. Muller and M. Bauer Justus Liebigs Ann. Chem. (1962), p. 92. Full Text via CrossRef

Tetrahedron Letters
Volume 27, Issue 2, 1986, Pages 219-222

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