Stereocontrolled synthesis of angularly fused tricyclic ring systems by means of 1-metalla-1,3,5-hexatrienes (M=Cr,W)

He-Ping Wu; Rudolf Aumann; Roland Frohlich; Birgit Wibbeling

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Stereocontrolled synthesis of angularly fused tricyclic ring systems by means of 1-metalla-1,3,5-hexatrienes (M=Cr,W)

机译：1-metalla-1,3,5-己三烯（M = Cr，W）的立体控制稠合三环系统的立体合成

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An efficient pathway for the stereocontrolled synthesis of functionalized,angularly fused tricyclic ring systems from readily available (1-alknyl)-carbene complexes [(OC)_5M=C(OEt)-C ident to CR](M=Cr,W;R-Ph,c-C_6H_9)is described.The synthesis involvesthe formation of a 1-metalla-1,3,5-hexatriene from the (1-alkynyl)carbene tungsten complex [(OC)_5W=C(OEt)C ident to C-c-C_6H_9]and a secondary amine,and its thermally induced #pi#-cyclization to a tetrahydroindene,which undergoes a spontaneous isomerization of these tetrahydroindenes withpyran-2-ylidene complexes derived from(1-alkynyl)carbene complexes [(OC)_5M=C-(OE_5)C ident to CPh](M=Cr,W)proceeds smoothly giving angularly fused tricyclic ring systems,rearrangementof which may generate spiro(cyclopentane-1,1-indanes)as side products.The synthesis is hyghly versatile and can be applied to the formation of various ring systems,such as steroid-type ring skeletons.

机译：从容易获得的（1-炔基）-卡宾配合物[（OC）_5M = C（OEt）-C等同于CR]（M = Cr，W; R）立体控制合成功能化的角稠合三环系统的有效途径描述了-Ph，c-C_6H_9）的合成。合成涉及从（1-炔基）卡宾钨配合物[（OC）_5W = C（OEt）C Cc-C_6H_9]和仲胺，将其热诱导＃pi＃-环化为四氢茚，然后将这些四氢茚与衍生自（1-炔基）卡宾配合物[（OC）_5M的吡喃-2-亚烷基配合物进行自发异构化= C-（OE_5）C等同于CPh]（M = Cr，W）平稳地产生有角度稠合的三环系统，其重排可能产生副产物螺（环戊烷-1,1-茚满）。该合成非常灵活并可用于形成各种环系统，例如类固醇型环骨架。

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来源
《Chemistry: A European journal》 |2002年第4期|共7页
作者
He-Ping Wu; Rudolf Aumann; Roland Frohlich; Birgit Wibbeling;
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正文语种 eng
中图分类化学;应用化学;
关键词
annulation; carbene ligands; cycloaddition; steroids; tungsten;

机译：环空;卡宾配体;环加成;类固醇;钨;

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1. Organic synthesis via transition-metal complexes. Part 114. Stereocontrolled synthesis of angularly fused tricyclic ring systems by means of 1-metalla-1,3,5-hexatrienes (M = Cr, W) [J] . Wu HP., Aumann R., Frohlich R., Chemistry: A European journal . 2002,第4期

机译：通过过渡金属络合物进行有机合成。第114部分：借助于1-金属-1,3,5-己三烯（M = Cr，W）的立体控制稠合三环系统的立体合成
2. Unusual fused tricyclic 2-azetidinones: Stereocontrolled synthesis of rigid dipeptide surrogates from beta-lactam-tethered imines via sequential cycloaddition/ring-closing metathesis [J] . Alcaide B., Alonso JM., Aly MF., Synlett . 2001,第6期

机译：不寻常的稠合三环2-氮杂环丁烷酮：通过顺序环加成/环合置换从β-内酰胺系亚胺立体控制合成刚性二肽替代物
3. Heterocycles with a bridgehead nitrogen atom.16.* Assembly of a peri-fused system from an angular tricycle by recyclization of an oxazole ring into pyrrole one [J] . E.V.Babaev, A.A.Tsisevich, D.V.Albov, Russian Chemical Bulletin . 2005,第1期

机译：具有桥头氮原子的杂环。16。*通过将恶唑环环化为吡咯，从角三轮车组装成近融合系统
4. A CAN-catalyzed sequential three component reaction for the one-pot synthesis of tricyclic fused pyrrole systems [C] . Veronica Estevez, Mercedes Villacampa, J. Carlos Menendez European Symposium on Organic Chemistry . 2009

机译：用于三环熔吡咯体系的单盆合成的甘蔗催化的连续三种组分反应
5. Synthesis of Novel Fused Tricyclic and Tetracyclic Skeletons Through Rhodium(I)-Catalyzed [2+2+2+1] Cycloaddition of Enediyne Derivatives with Carbon Monoxide. [D] . Kaloko, Joseph Junior. 2010

机译：铑（I）催化烯属衍生物与一氧化碳环加成的[2 + 2 + 2 + 1]环加成反应合成新颖的稠合三环和四环骨架。
6. Design and Synthesis of Highly Potent HIV-1 Protease Inhibitors Containing Tricyclic Fused Ring Systems as Novel P2-ligands: Structure-Activity Studies Biological and X-ray Structural Analysis [O] . Arun K. Ghosh, Prasanth R. Nyalapatla, Satish Kovela, -1

机译：包含三环融合环系统作为新型P2-配体的高强度HIV-1蛋白酶抑制剂的设计与合成：结构活性研究生物学和X射线结构分析
7. Dicobaltoctacarbonyl species in organic synthesis : a novel route into tricyclic fused ring systems [O] . Wilkins Derek 2009

机译：有机合成中的二钴羰基物种：进入三环稠环系统的新途径
8. Synthesis and Ab Initio Structure Determination of Zn4O(BO3)2, a Microporous Zincoborate Built Up From 'Fused' 3-Ring and 5-Ring Sub-Units. [R] . Harrison, W. T., Gier, T. E., Stucky, G. D. 1993

机译：Zn4O（BO3）2的合成和从头构型测定，由“稠合”3环和5环亚单元构成的微孔硼酸盐。

Stereocontrolled synthesis of angularly fused tricyclic ring systems by means of 1-metalla-1,3,5-hexatrienes (M=Cr,W)

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