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Syntheses of Anthracyclines and Fredericamycin A via Strong Base-Induced Cycloaddition Reaction of Homophthalic Anhydrides

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Anthracycline Chemistry and Biology I

Part of the book series: Topics in Current Chemistry ((TOPCURRCHEM,volume 282))

Abstract

Strong base-induced cycloaddition reactions of homophthalic anhydrides with quinone derivatives affordperi-hydroxyl aromatic compounds in a regioselective manner. Thereactions have been applied to the syntheses of biologically important natural products. This review focuseson the following topics: (i) preparation of homophthalic anhydrides from homophthalic acids using(trimethylsilyl)ethoxyacetylene, (ii) strong base-induced cycloaddition of homophthalic anhydrideswith the carbon–carbon double bond and the reaction mechanism, especially addressing the regiochemistryof the reaction, and (iii) application of the reaction to the efficient asymmetric syntheses of anthracyclinesand fredericamycin A.

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Authors and Affiliations

  1. Graduate School of Pharmaceutical Sciences, Osaka University, 1–6 Yamadaoka, Suita, 565-0871, Osaka, Japan

    Yasuyuki Kita & Hiromichi Fujioka

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  1. Yasuyuki Kita
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  2. Hiromichi Fujioka
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Correspondence to Yasuyuki Kita .

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Karsten Krohn

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Kita, Y., Fujioka, H. (2007). Syntheses of Anthracyclines and Fredericamycin A via Strong Base-Induced Cycloaddition Reaction of Homophthalic Anhydrides. In: Krohn, K. (eds) Anthracycline Chemistry and Biology I. Topics in Current Chemistry, vol 282. Springer, Berlin, Heidelberg. https://doi.org/10.1007/128_2007_10

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