Total Synthesis of Naturally Occurring Quinones

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  • 天然産キノンの合成研究
  • テンネンサン キノン ノ ゴウセイ ケンキュウ

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Abstract

New syntheses of naturally occurring quinones with high physiological activities are described in this review. Synthetic strategies of these quinones are based on the regio- (and/or stereo-) selective introduction of allylic or 2, 4-pentadienyl side chains directly to quinones with the corresponding organosilanes and -stannanes. This review contains the following topics; (i) allylorganostannanes as efficient allylating reagents to quinones, and regio- and stereoselective synthesis of polyprenylquinones, i. e. coenzyme Qn, vitamin K, (ii) methyl 2-triorganosily1-3-butenoate as a new synthon of 3-methylcarbonylallyl anion and its application to the synthesis of pyranonaphthoquinone antibiotics, i. e. (±) -nanaomycin A, (±) -deoxyfrenolicin, (iii) biomimetic AB ring synthesis of an aglycone of an anthracycline antibiotic, aklavinone, by means of intramolecular electron relay system, (iv) synthesis of 11-deoxydaunomycinone precursor by means of intramolecular Diels-Alder reaction, (v) novel synthesis of pyrrolo [1, 2-a] -indol-5, 8-quinone by means of intramolecular cyclization and application to the synthesis of mitosenes.

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