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Tetrahedron Letters | 1985

Denticulatolide, an ichthyotoxic peroxide-containing cembranolide from the soft coral Lobophytum denticulatum

Yasuto Uchio; Shizuko Eguchi; J. Kuramoto; Mitsuru Nakayama; Tsunao Hase

Abstract Denticulatolide, an ichthyotoxic cembranoid diterpene bearing acetoxy, α-methylene γ-lactone, and cyclic peroxide functions, has been isolated from the soft coral Lobophytum denticulatum. The structure (1) has been determined by spectral and chemical evidence and X-ray crystallographic method.


Tetrahedron Letters | 1980

Labdane diterpene glycosides with 6-deoxy-L-idose from Aster spathulifolius Maxim.

Yasuto Uchio; M. Nagasaki; Shizuko Eguchi; Akihiko Matsuo; Mitsuru Nakayama; Shûichi Hayashi

Abstract Three labdane type diterpene glycosides ( 1 , 2 and 3 ) with 6-deoxy-L-idose have been isolated from Aster spathulifolius Maxim. and their structures have been determined on the basis of chemical and spectral data.


Nippon Kagaku Kaishi | 1973

Mass Spectra of Halkendin and Its Derivatives

Mitsuru Nakayama; Shizuko Eguchi; Akihiko Matsuo; Shûichi Hayashi; Shinzaburo Hishida; Yoshiaki Kato

The mass spectra of 4-methoxy (6), 3, 4-dimethoxy (halkendin) (1), 4-ethoxy-3-methoxy (12) furo(3, 2: 6, 7)coumarin, and their 2, 3 dihydrocompounds (7, 8, 13) are recorded in Figs.1, 3, 4, 6 and 7. The fragmentation is discussed on the basis of high resolution data, metastable ion evidences, and deuterium labelling studies (Tables ltv8 and Figs.2, 5, 9 and 10).The spectrum of halkendin (Z) shows a major breakdown pathway involving initial loss of a methyl radical from Cs methoxy group followed by expulsion of CQ, then successive loss of CO, CH3(C4), and CO(Fig.5).4-Ethoxycoumarin 12 shows Ioss of ethylene om C, side chain giving an ion m/e 232 whose further fragmentation is very similar to that of 4-hydroxycoumarin derivatives (Fig.10). op.It is shown that significant structural information can be obtained from the mass spectra of 3, 4-dialkoxyfurocoumarins.


Chemistry Letters | 1982

THE ISOLATION OF TWO SIMPLE γ-LACTONIC CEMBRANOLIDES FROM THE SOFT CORAL SINULARIA MAYI

Yasuto Uchio; Shizuko Eguchi; Mitsuru Nakayama; Tsunao Hase


Journal of Mass Spectrometry | 1979

Hydrogen transfer in the retro diels–alder fragmentation of oxygen-containing heterocyclic compounds. II—Chromones

Shizuko Eguchi


Journal of Mass Spectrometry | 1977

The formation of a resonance stabilized oxonium ion in isoflavone and 2′‐substituted isoflavones

Shizuko Eguchi; Machiko Haze; Mitsuru Nakayama; Shûichi Hayashi


Journal of Mass Spectrometry | 1978

Hydrogen transfer in the retro Diels-Alder fragmentation of oxygen-containing heterocyclic Compounds. I—chromanones and 4-hydroxychromans

Shizuko Eguchi


Bulletin of the Chemical Society of Japan | 1978

The synthesis of neobavaisoflavone and related compounds.

Mitsuru Nakayama; Shizuko Eguchi; Shûichi Hayashi; Masao Tsukayama; Tokunaru Horie; Toshihide Yamada; Mitsuo Masumura


Journal of Mass Spectrometry | 1977

Expulsion of the CHO radical from the molecular ion of homochromones

Mitsuru Nakayama; Hiroshi Yamaoka; Shizuko Eguchi; Terukiyo Hanafusa; Shûichi Hayashi


Journal of Mass Spectrometry | 1976

Fragmentation in doubly charged ion mass spectra of anhydropisatin and related compounds

Shizuko Eguchi; Mitsuru Nakayama; Shûichi Hayashi

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