Diastereoselective opening of trisubstituted epoxy alcohols: Application in the studies directed toward the synthesis of octenoic acid moiety of cryptophycins

Tushar K. Chakraborty; Sanjib Das

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Diastereoselective opening of trisubstituted epoxy alcohols: Application in the studies directed toward the synthesis of octenoic acid moiety of cryptophycins

机译：三取代环氧醇的非对映选择性打开：在针对隐藻霉素辛烯酸部分合成的研究中的应用

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Stereoselective synthesis of the 5,7-acetonide of (2E, 5S, 6R, 7R, 8R)-5, 7, 8-trihydroxy-6-methyl-8-phenyl-2-octenoic acid ethyl ester (3), an isomer of 2, precursor of the epoxy octenoic acid moiety 1 present in depsipeptide cryptophycins is achieved where diastereoselective opening of an intermediate trisubstituted epoxy alcohol 4 based on a radical-mediated method developed by us earlier furnishes the crucial '2-methyl-1, 3-diol' moiety of the C_5-C_7 segment of the molecule. The protocol also allows the synthesis of some of the other 16 diasteromers of this hydroxy acid having 4 chiral centres which can find useful applications in the structure-activity relationship (SAR) studies of these potent antitumor agents.

机译：（2E，5S，6R，7R，8R）-5、7、8-三羟基-6-甲基-8-苯基-2-辛烯酸乙酯（3）的5,7-丙酮化物的立体选择性合成在二肽隐藻霉素中存在的环氧辛烯酸部分1的前驱体中，通过基于我们先前开发的自由基介导方法的中间体三取代环氧醇4的非对映选择性打开提供了至关重要的'2-甲基-1，3-分子的C 5 -C 7链段的“二醇”部分。该方案还允许合成具有4个手性中心的此羟基酸的其他16个非对映异构体，这些化合物可以在这些有效抗肿瘤剂的结构活性关系（SAR）研究中找到有用的应用。

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《Journal of the Indian Chemical Society》 |1999年第12期|共6页
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Tushar K. Chakraborty; Sanjib Das;
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中图分类化学;
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1. Diastereoselective opening of trisubstituted epoxy alcohols: Application in the studies directed toward the synthesis of octenoic acid moiety of cryptophycins [J] . Tushar K. Chakraborty, Sanjib Das Journal of the Indian Chemical Society . 1999,第11a12期

机译：三取代环氧醇的非对映选择性打开：在针对隐藻霉素辛烯酸部分合成的研究中的应用
2. The direct and highly diastereoselective synthesis of 3,4-epoxy-2-piperidones. Application to the total synthesis and absolute configurational assignment of 3α,4α-epoxy-5β-pipermethystine [J] . Urbano Osorio-Nieto, Laura Y. Vazquez-Amaya, Herbert Hoepfl, Organic & biomolecular chemistry . 2018,第1期

机译：3,4-环氧-2-哌啶酮的直接和高度非对映选择性合成。在3α，4α-环氧-5β-哌丁菊酯的全合成及绝对构型分配中的应用
3. Highly Enantio- and Diastereoselective One-Pot Synthesis of Acyclic Epoxy Alcohols and Allylic Epoxy Alcohols [J] . Ann Rowley Kelly, Alice E.Lurain, Patrick J.Walsh Journal of the American Chemical Society . 2005,第42期

机译：无环环氧醇和烯丙基环氧醇的高度对映和非对映选择性一锅合成
4. Microwave synthesis of 2,3,5-trisubstituted-1,3-imidazolidin-4-ones bearing 1,3,4-oxadiazole moiety and preliminary evaluation of their antibacterial activity [C] . Zeid Hassan Abood, Hayder Raheem Ali, Hussein Ali Qabel International Conference on Applied Science and Technology . 2019

机译：微波合成2,3,5-三取代-1,3-咪唑烷-4-轴承1,3,4-氧代唑部分，对其抗菌活性的初步评估
5. The attempted synthesis of teucrolivin A via the oxy-Cope/Claisen/ene reaction: Diastereoselective formation of quaternary centers directed by macrocyclic conformation and its application to the formal synthesis of (-)-mesembrine. [D] . Arns, Steve. 2008

机译：尝试通过oxy-Cope / Claisen / ene反应合成teucrolivin A：由大环构象指导的季中心的非对映选择性形成及其在（-）-membrine形式合成中的应用。
6. Synthesis of Tetrahydropyridazines by a Metal-carbene Directed Highly Enantioselective Vinylogous N-H Insertion/Lewis Acid Catalyzed Diastereoselective Mannich Addition [O] . Dr. Xinfang Xu, Dr. Peter Y. Zavalij, Prof. Michael P. Doyle -1

机译：用金属 - 甲基甲基指导高度映选择性乙烯基N-H插入/路易斯酸催化的二氢吡啶的合成
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机译：高肾上腺素和非对抗的一罐合成无环环氧醇和烯丙基环氧醇

Diastereoselective opening of trisubstituted epoxy alcohols: Application in the studies directed toward the synthesis of octenoic acid moiety of cryptophycins

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