Concepedia

The efficient and regioselective synthesis of the naphthoquinone core of streptovaricin U

Masaaki Miyashita, Takahiro Yamasaki, Tomonori Shiratani, Susumi Hatakeyama, Masahiro Miyazawa, Hiroshi Irie

Chemical Communications · 1997 · 17 citations · 10 references

DOI

Concepts

Abstract

The efficient and regioselective synthesis of the naphthoquinone core of streptovaricin U 1 via the Diels–Alder reaction of 1-methoxy-2-methyl-3-trimethylsilyloxybuta-1,3-diene 5 with the 2,6-dibromo-3-methyl-1,4-benzoquinone 6 is described.

References

10

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Stereospecific methylation of .gamma.,.delta.-epoxy acrylates by trimethylaluminum: a method for the iterative construction of polypropionate chains

Masaaki Miyashita, M. HOSHINO, Akira Yoshikoshi · The Journal of Organic Chemistry · 1991 · 89 citations

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Dipyranoside precursors for ansamycins. Pyranosidic homologation. 5

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A synthesis of the naphthalene core of streptovaricin D via A synthon of NH2+

Barry M. Trost, William H. Pearson · Tetrahedron Letters · 1983 · 34 citations

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Chemistry and biochemistry of the streptovaricins. XV. Protostreptovaricins I-V

Prabhakar V. Deshmukh, John J. Ameel, Kenneth L. Rinehart et al. · Journal of the American Chemical Society · 1976 · 31 citations

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