Trangmolins A–F with an Unprecedented Structural Plasticity of the Rings A and B: New Insight into Limonoid Biosynthesis,Chemistry - A European Journal

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Trangmolins A–F with an Unprecedented Structural Plasticity of the Rings A and B: New Insight into Limonoid Biosynthesis
Chemistry - A European Journal ( IF 3.9 ) Pub Date : 2016-07-07 , DOI: 10.1002/chem.201602230
Wanshan Li ₁ , Li Shen ₁ , Torsten Bruhn ₂ , Patchara Pedpradab ₃ , Jun Wu ₁ , Gerhard Bringmann ₂

Affiliation

The absolute stereostructures of trangmolins A–F (1–6), limonoids with three new and one known topologies of the rings A and B, were unambiguously determined by NMR spectroscopic investigations, single‐crystal XRD analysis, and quantum‐chemical electronic circular dichroism calculations. Compounds 1–3 contain a hexahydro‐1H‐inden‐4‐one motif, compound 4 comprises a hexahydro‐2,6‐methanobenzofuran‐7‐one cage, and compound 5 consists of a hexahydro‐2H‐2,8‐epoxychromene scaffold. The C1−C30 linkage in 1–3 and the C3−C30 connection in 4 form two unprecedented types of ring A/B‐fused carbobicyclic cores: viii and ix. The oxidative cleavage of the C2−C3 bond in 5 and heterocyclization in 4 and 5 constitute the unprecedented tricyclic 6/6/5 ring A/B¹/B²‐ and 6/5/6 ring A¹A²/B‐fused topologies, respectively, which are uncovered, for the first time, in the construction of limonoid architectures. The diverse cyclization patterns of 1–6 reveal an unparalleled structural plasticity of rings A and B in limonoid biosynthesis.

中文翻译：

具有前所未有的环A和B结构可塑性的Trangmolins A–F：对柠檬苦素生物合成的新见解

通过NMR光谱研究，单晶XRD分析和量子化学电子圆二色性，明确确定了trangmolins A–F（1 – 6），具有A环和B环的三个新拓扑结构和一种已知拓扑结构的柠檬苦素类化合物的绝对立体结构。计算。化合物1 - 3包含六氢ħ茚-4-酮基序，化合物4只包括一个六氢-2,6- methanobenzofuran -7-酮笼，和化合物5由一个六氢的2H -epoxychromene -2,8-脚手架。所述C1-C30连杆在1 - 3，并在C3-C30连接4形成了两个前所未有的A / B环稠合碳双环核类型：viii和ix。5中的C2-C3键的氧化裂解以及4和5中的杂环化构成了前所未有的三环6/6/5环A / B ¹ / B ^2-和6/5/6环A ¹ A ² / B-稠合分别在柠檬黄素体系结构的构建中首次发现的拓扑。1 – 6的各种环化模式表明柠檬苦素类生物合成中环A和环B具有无与伦比的结构可塑性。

更新日期：2016-07-07

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