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Pyranonaphthoquinone계 항생제 Nanaomycin A의 합성
趙仁鎬,魯永釗,柳東辰 全北大學校 1989 論文集 Vol.31 No.-
An efficient synthesis of 8-benzyloxy-6-phenylsulfonyl-3-octen-2-one(48), the Michael acceptor necessary to prepare nanaomhycin A(la) was accomplished via seven step reaction sequence using ethylacrylate(53) as the starting material. Thus, a Michael reaction of thiophenoxide with ethylacrylate gave 3-(phenylthio) propionate(54), which was reduced to propanol 55, and then converted to 3-(acetoxy) propylphenylsulfide(56). Oxidation of the sulfide 56 with mCPBA as an oxidizing agent gave sulfone 57. Anion of the sulfone 57 generated by using LDA was treated with chloroacetalde-hydedimethylacetal to provide dimethoxypenthanol 58. Benzylation of the alcohol 58, followed by acid catalyzed hydrolysis of the dimethoxy function gave pentanal 59. Wittig reaction of the pentanal 59 with triphenyphosphoranylidene-2-propanone purnish 3-octen-2 on 48.
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새로운 Morindaparvin A 유도체들의 합성 (Ⅱ)
박시호,로영쇠,권윤자,강흔수,조인호,Park, Si Ho,Rho, Young S.,Kwon, Yoon Ja,Kang, Heun Soo,Cho, In Ho 대한화학회 1995 대한화학회지 Vol.39 No.3
이미 합성하여 보고한 1,2-Dihydroxyanthraquinone 유도체(9, 10)에 매우 간편하고 효율적인 방법으로 $-N(CH_3)_2,\;-OMe,\;-NH_2,\;-COOH,\;-CHClC(O)NH_2,\;-CHClCH_2OH,\;-CHClC(O)CH_3$ 등이 붙은 여러 종류의 새로운 Morindaparvin A(2~8)의 유도체를 합성하였다. A simple and efficient synthesis of new kind of Morindaparvin A derivatives (2~8) containing $-N(CH_3)_2,\;-OMe,\;-NH_2,\;-COOH,\;-CHClC(O)NH_2,\;-CHClCH_2OH\;and\;-CHClC(O)CH_3$ was completed with the reported 1,2-dihydroxyanthraquinone derivatives (9, 10).
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