Exploration of the diastereoselectivity in an unusual Grignard reaction and its application towards the synthesis of styryl lactones 7-epi-(+)-goniodiol and 8-epi-(?)-goniodiol

Subhash P. Chavan; Harshali S. Khatod; Tamal Das; Kumar Vanka

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Exploration of the diastereoselectivity in an unusual Grignard reaction and its application towards the synthesis of styryl lactones 7-epi-(+)-goniodiol and 8-epi-(?)-goniodiol

机译：探讨异映选择在不寻常的格子反应中的探讨及其朝向STYRYL乳烯酮7-EPI - （+） - 碘醇和8-EPI - （α） - 腺苷的合成

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An unusual diastereoselective Grignard reaction is explored, where the Grignard reagents are derived from 1, n -dihaloalkanes. A steric bias due to the presence of a quaternary centre adjacent to the acetonide ester at the benzylic position is responsible for the formation of an intramolecularly reduced product in almost quantitative yield. This steric hindrance is responsible for the diastereoselectivity observed with a variety of aromatic as well as aliphatic esters. The unusual Grignard reaction furnishes long chain secondary alcohols possessing a terminal olefin, which are synthetically important intermediates. As an application of this method, the diastereoselective synthesis of styryl lactones viz. 7- epi -(+)-goniodiol ( 29 ) and 8- epi -(?)-goniodiol ( 30 ) has been achieved.

机译：探索了一种不寻常的非对映选择性的格子反应，其中格氏试剂衍生自1，N-二卤烷烃。由于邻近苄基位置的乙酸酯酯的季度中心的存在而导致的空间偏差负责以几乎定量的产率形成分子内降低的产物。该空间障碍负责用各种芳族和脂族观察到的非对映选择性。不寻常的格氏反应提供具有末端烯烃的长链二次醇，它们是合成重要的中间体。作为这种方法的应用，甾烷基乳酸酯Qiz的非对映选择性合成。 7- EPI - （+） - 促碘（29）和8- EPI - （α） - 达碘（30）已经实现。

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《RSC Advances》 |2016年第56期|共5页
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Subhash P. Chavan; Harshali S. Khatod; Tamal Das; Kumar Vanka;
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1. Exploration of the diastereoselectivity in an unusual Grignard reaction and its application towards the synthesis of styryl lactones 7-epi-(+)-goniodiol and 8-epi-(-)-goniodiol [J] . Chavan Subhash P., Khatod Harshali S., Das Tamal, RSC Advances . 2016,第56期

机译：探索异映选择在不寻常的格子反应中的探讨及其朝向STYRYL乳酰胺的合成7-EPI - （+） - （+） - （+） - （+） - （ - ） - 碘醇
2. Total Synthesis and Cytotoxicity of (+)-and (-)-Goniodiol and 6-epi-Goniodiol.Construction of alpha,beta-Unsaturated Lactones by Ring-Closing Metathesis [J] . Katsuyuki Nakashima, Naoki Kikuchi, Daisuke Shirayama Bulletin of the Chemical Society of Japan . 2007,第2期

机译：（+） - 和（ - - ） - 碘二醇和6-细胞毒性的总合成和细胞毒性α，β-不饱和乳酰胺的闭环复分解
3. Stereocontroled Syntheses of Novel Styryl Lactones,(+)-Goniodiol,(+)-Goniotriol,(+)-8-Acetylgoniotriol,(+)-Goniofufurone, (+)-9-Deoxygoniopypyrone,(+)-Goniopypyrone, and (+)-Altholactone from Common Intermediates and Cytotoxicity of Their Congener [J] . Tsubuki Masayoshi Tetrahedron . 1999,第9期

机译：新型苯乙烯基内酯，（+）-壬二醇，（+）-壬三醇，（+）-8-乙酰基goniotriol，（+）-Goniofufurone，（+）-9-Deoxygoniopypyrone，（+）-Goniopyrone和（++）的立体控制合成）-普通内酯中的内酯及其同源物的细胞毒性
4. UNUSUAL REACTION OF GRIGNARD REAGENTS TOWARDS FLUOROALKYLATED ESTERS [C] . Takashi Yamazaki, Tsukasa Terajima Treatise Gist Anthology . 2007

机译：RIG剂对氟代烷基化酯的反常反应
5. New avenues and applications for parallel library synthesis: I. Application of multicomponent reactions for the efficient synthesis of small molecule macroarrays. II. Characterization of non-native N-acylated L-homoserine lactones as bacterial biofilm inhibitors [D] . Lin, Qi 2007

机译：平行文库合成的新途径和应用：I.多组分反应在小分子大分子阵列有效合成中的应用。二。非天然N-酰化L-高丝氨酸内酯作为细菌生物膜抑制剂的表征
6. Three-Component Coupling Reactions of Silyl Glyoxylates Vinyl Grignard Reagent and Nitroalkenes: An Efficient Highly Diastereoselective Approach to Nitrocyclopentanols [O] . Gregory R. Boyce, Jeffrey S. Johnson -1

机译：甲硅烷基甲氧化甲硅烷基乙烯基格氏试剂和Nitroallenes的三组分偶联反应：对硝化萘酚的有效高度不映射的方法
7. Efficient synthesis of the styryllactones, (+)-goniothalamin, (+)-7-epi-goniodiol and (+)-9-deoxygoniopypyrone [O] . Liu ZY, Ji JX, Li BG 2004

机译：苯乙烯基内酯，（+）-角硫胺素，（+）-7-表-goniodiol和（+）-9-脱氧goniopypyrone的高效合成
8. Reactions between Alkyl Grignard Reagents and Aminophosphazenes Synthesis of Alkyl-chloro-cyclotriphosphazenes [R] . Allcock, H. R., Desorcie, J. L., Wagner, L. J. 1984

机译：烷基格氏试剂与氨基磷腈的反应合成烷基氯 - 环三磷腈

Exploration of the diastereoselectivity in an unusual Grignard reaction and its application towards the synthesis of styryl lactones 7-epi-(+)-goniodiol and 8-epi-(?)-goniodiol

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