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Journal of the Korean Chemical Society (JKCS)

ISSN 1017-2548(Print)
ISSN 2234-8530(Online)
Volume 37, Number 1
JKCSEZ 37(1)
February 20, 1993 

Total Synthesis of 6-Deoxybisanhydrodaunomycinone Anticancer Antibiotics

항암항생제 6-Deoxybisanhydrodaunomycinone의 합성
In Ho Cho, Young Soy Rho, Si Ho Park, Koo Hyeon Ahn, Hong Sig Sin, Byoung Ku Han

조인호, 노영소, 박시호, 안구현, 신홍식 ,한병구
항암항생제 Danuorubicin(1b)의 aglycone인 daunomycinone의 전이물질 6-deoxybisanhydrodaunomycinone(20)의 전 합성이 이루어졌다. 만들어진 enone 화합물 4를 phthalide sulfone 7과 반응시킨 뒤 oxidation과 methylation을 시켜서 anthraquinone 화합물 10을 얻었다. 화합물 10의 benzyl기를 bromination시켜서 얻은 monobromo 화합물 11을 bis(tetrabutylammonium) dichromate로 고리화반응을 시켜서 hydroxyanthraquinone 화합물 16을 얻은 뒤 OH기를 thiophenol로 치환시켰다. sulfide 화합물 17은 phosphate buffer 용액속에서 m-CPBA로써 산화시켜서 anthraquinonyl sulfone 화합물 18을 얻은 뒤 methyl vinyl ketone(19)과 결합시켜서 화합물 20을 얻었다.

A brief route for total synthesis of 6-deoxybisanhydrodaunomycinone(20) was described, namely the precursor of the daunomycinone, the aglycone of the anticancer antibiotic daunorubicin (1b). The prepared enone 4 was condensed with phthalide sulfone 7 to afford anthraquinone 10 after oxidation and methylation. The benzylic group of 10 was brominated, and subsequent oxidation with bis(tetrabutylammonium) dichromate followed by cyclization give hydroxyanthraquinone 16, which was displaced with thiophenol. Oxidation of 17 with m-CPBA in phosphate buffer solution afforded anthraquinonyl sulfone 18 which was condensed with methyl vinyl ketone (19) to furnish 20.

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