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首页> 外文学位 >Total synthesis of (+/-)-phloeodictine A1, a novel biomimetic route to the 3-acyl-5-hydroxy-3-pyrrolin-2-one and 3-acyl-3,4-epoxy-5-hydroxypyrrolidin-2-one ring systems and syntheses of ficuseptine, juliprosine, and juliprosopine.
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Total synthesis of (+/-)-phloeodictine A1, a novel biomimetic route to the 3-acyl-5-hydroxy-3-pyrrolin-2-one and 3-acyl-3,4-epoxy-5-hydroxypyrrolidin-2-one ring systems and syntheses of ficuseptine, juliprosine, and juliprosopine.

机译：（+/-）-邻苯二酚A1的全合成，这是一种新型的仿生路线，可以合成3-酰基-5-羟基-3-吡咯啉-2-酮和3-酰基-3,4-环氧-5-羟基吡咯烷酮-2-一环系统和榕树素，菊酯碱和菊酯碱的合成。

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摘要

The antitumor antibiotic phloeodictine A1 has been synthesized by a convergent seven-step route in 8% overall yield. The key step was the Eguchi aza-Wittig reaction of the azide to give furan protected amidine followed by a retro Diels-Alder reaction to liberate amidine. Addition of 11-dodecenylmagnesium bromide to the amidine gave the C-6 alkylated amidine of the phloeodictine A1 core, alkylation with the bis Boc-protected guanidino iodide and deprotection completed the first synthesis of phloeodictine A1.; Modified Moffat oxidation of primary alcohols of phenylalaninol or prolinol afforded aldehydes that underwent intramolecular aldol reactions on treatment with a NaOH solution to yield 4-pyrrolin-2-ones. Oxidation with DMDO at -40°C provided 3-acyl-5-hydroxy-3-pyrrolin-2-ones with the ring system of oteromycin, UCS 1025A, and related natural products. Further oxidation of the 3-acyl-5-hydroxy-3-pyrrolin-2-one yielded 3-acy1-3,4-epoxy-5-hydroxy-pyrrolidin-2-one with the ring system of fusarin C and epolactaene. Dehydration of 3-acyl-5-hydroxy-3-pyrrolin-2-one afforded the dime compound with the talaroconvolutin A ring system.; Biomimetic intramolecular Chichibabin pyridine syntheses using two molecules of an aldehyde and 4-aminobutanal dimethyl acetal proceed efficiently in AcOH at 95°C to give 2,3-dihydro-1H-indolizinium salts. Reaction occurs at 25°C if 1-pyrroline is used instead of 4-aminobutanal dimethyl acetal. This reaction has been used for a one step synthesis of ficuseptine and the first syntheses of juliprosine and juliprosopine, which is now assigned as the trans stereoisomer.
机译：已通过收敛的七步路线合成了抗肿瘤抗生素Phophodictine A1，总产率为8％。关键步骤是叠氮化物的Eguchi aza-Wittig反应，得到呋喃保护的am，然后进行逆Diels-Alder反应，释放出idine。将11-十二碳烯基溴化镁加到the上，得到邻苯二甲A啶A1核心的C-6烷基化with，用双Boc保护的胍基碘化物烷基化并脱保护完成了邻苯二甲A啶A1的第一次合成。苯丙氨醇或脯氨醇的伯醇的改性莫法（Moffat）氧化制得的醛在用NaOH溶液处理后会发生分子内羟醛反应，生成4-吡咯啉-2-酮。在-40°C下用DMDO氧化可得到3酰基5-羟基3-吡咯啉2-酮与奥特霉素，UCS 1025A和相关天然产物的环系统。 3-酰基-5-羟基-3-吡咯啉-2-酮的进一步氧化，生成了带有富沙林C和上半碳烯的环系统的3-acy1-3,4-环氧-5-羟基-吡咯烷酮-2-酮。 3-酰基-5-羟基-3-吡咯啉-2-酮的脱水得到具有talaroconvolutin A环系统的角钱化合物。使用两分子醛和4-氨基丁醛二甲基乙缩醛的仿生分子内chichibabin吡啶合成在95°C的AcOH中有效进行，得到2,3-二氢-1H-吲哚并鎓盐。如果使用1-吡咯啉代替4-氨基丁醛二甲基乙缩醛，则反应在25℃发生。该反应已被用于一步一步合成榕树素和最初合成的芥子油素和芥子油品的合成，现在被指定为反式立体异构体。

著录项

  • 作者

    Neubert-Langille, Bobbianna J.;

  • 作者单位

    Brandeis University.;

  • 授予单位 Brandeis University.;
  • 学科 Chemistry Organic.
  • 学位 Ph.D.
  • 年度 2005
  • 页码 143 p.
  • 总页数 143
  • 原文格式 PDF
  • 正文语种 eng
  • 中图分类 有机化学;
  • 关键词

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