The Discreet Structural Diversity of Briarellins: DU8+ Guided Multiple Structure Revisions Yielded Two Unknown Structural Types
The Discreet Structural Diversity of Briarellins: DU8+ Guided Multiple Structure Revisions Yielded Two Unknown Structural Types
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Briarellins 的谨慎结构多样性：DU8 引导的多重结构修改产生了两种未知的结构类型
DOI：
10.1021/acs.joc.0c00555
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发表时间：
2020
期刊：
影响因子：
--
通讯作者：
Kutateladze, Andrei G.
中科院分区：
文献类型：
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作者：
Holt, Tina A.;Reddy, D. Sai;Huple, Deepak B.;West, Lyndon M.;Rodríguez, Abimael D.;Crimmins, Michael T.;Kutateladze, Andrei G.
Briarellins是C2-C11环化西莫林的一个子集，被认为含有C3-C14醚或内酯桥，类似于石棉。然而，对灯盏花素J建议结构的全合成揭示了一个错误的分配。我们利用最近发展的密度泛函/参数混合方法DU8+对Briarellin进行了重新计算，并将Briarellin C14-C3ε-内酯的结构修改为包含C14-C11或C14-C12内酯桥的新结构类型。确定了灯盏花素和石棉醚的原始结构。
Briarellins, a subset of C2–C11 cyclized cembranoids, were proposed to contain a C3–C14 ether or lactone bridge, similar to asbestinins. However, the total synthesis of the proposed structure of briarellin J revealed a misassignment. We revisited briarellins, computationally, with the help of a recently developed hybrid DFT/parametric method, DU8+, and revised the structures of briarellin C14–C3 ε-lactones to new structural types containing either a C14–C11 or C14–C12 lactone bridge. The original structures of briarellin and asbestinin ethers were confirmed.