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Synthesisof a des-B-Ring BryostatinAnalogue Leads to an Unexpected Ring Expansion of the BryolactoneCore

机译：合成-B-环类生长抑素类比导致溴内酯的意外环扩核心

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摘要

A convergent synthesis of a des-B-ring bryostatin analogue is described. This analogue was found to undergo an unexpected ring expansion of the bryolactone core to generate the corresponding 21-membered macrocycle. The parent analogue and the ring-expanded product both displayed nanomolar binding affinity for PKC. Despite containing A-ring substitution identical to that of bryostatin 1 and displaying bryostatin-like biological function, the des-B-ring analogues displayed a phorbol-like biological function in cells. These studies shed new light on the role of the bryostatin B-ring in conferring bryo-like biological function to bryostatin analogues.

机译：描述了des-B-环溴代他汀类似物的收敛合成。发现该类似物经历了溴代内酯核的意外的环膨胀，以产生相应的21元大环。母体类似物和环扩产物均显示出对PKC的纳摩尔结合亲和力。尽管含有与bryostatin 1相同的A环取代并显示出与bryostatin相似的生物学功能，des-B环类似物在细胞中仍显示出与佛波醇类似的生物学功能。这些研究揭示了bryostatin B环在赋予bryostatin类似物类似bryo的生物学功能中的作用。

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期刊名称 ACS AuthorChoice
作者
MatthewB. Kraft; ⊥; Yam B. Poudel; ∥; Noemi Kedei; NancyE. Lewin; Megan L. Peach; Peter M. Blumberg; Gary E. Keck; *;
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年(卷),期 -1(136),38
年度 -1
页码 13202–13208
总页数 7
原文格式 PDF
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专利

1. Synthesis of a des-B-Ring Bryostatin Analogue Leads to an Unexpected Ring Expansion of the Bryolactone Core [J] . Matthew B. Kraft, Yam B. Poudel, Noemi Kedei, Journal of the American Chemical Society . 2014,第38期

机译：des-B-环类生长抑素类似物的合成导致溴代内酯核的意外环扩
2. Unexpected Hydrolysis of a C(7)-Oxo-Substituted 2-Oxonorborn-1-yl Triflate: Norbornane-Ring Expansion versus Norbornane-Ring Contraction [J] . Antonio Garcia Martinez, Enrique Teso Vilar, Amelia Garcia Fraile, European journal of organic chemistry . 2002,第22期

机译：意外的C（7）-Oxo取代的2-Oxonorborn-1-yl Triflate的水解：降冰片环环膨胀与降冰片环收缩
3. Unexpected Ring Expansion of a Four-Membered Cyclophosphazane [J] . Besli Serap, Balci Ceylan Mutlu, Canturk Hakan, Inorganic Chemistry: A Research Journal that Includes Bioinorganic, Catalytic, Organometallic, Solid-State, and Synthetic Chemistry and Reaction Dynamics . 2016,第16期

机译：四元环磷氮烷的意外环扩
4. Single Lead ECG-based Ventricular Repolarization Classification for Early Identification of Unexpected Ventricular Fibrillation* [C] . Dakun Lai, Yifei Zhang, Xinshu Zhang Annual International Conference of the IEEE Engineering in Medicine and Biology Society . 2020

机译：基于单导心电图的心室复极化分类，可早期识别出意外的心室纤颤*
5. Novel aspects of epimetalation in organic synthesis A. Homo- and hetero- coupling of pi-bonded organic substrates via epititanation. B. Ring contraction of diazocines by epimetalation with alkali metal reductants and ring re-expansion by SET oxidants. [D] . Liu, Wei. 2013

机译：有机合成中表观金属化的新方面A. pi-键合的有机底物通过表观电化的均相和异相偶联。 B.通过用碱金属还原剂进行金属外延重氮重氮化合物的环收缩，并通过SET氧化剂使环再膨胀。
6. Synthesisof seco-B-Ring BryostatinAnalogue WN-1 via C–C Bond-Forming Hydrogenation: CriticalContribution of the B-Ring in Determining Bryostatin-like andPhorbol 12-Myristate 13-Acetate-like Properties [O] . Ian P. Andrews, John M. Ketcham, Peter M. Blumberg, -1

机译：合成B环丁环抑素的研究通过C–C键形成加氢的类似物WN-1：关键B环在确定类Bryostatin和蛋白中的作用佛波12-肉豆蔻酸酯13-醋酸酯样性质
7. Unexpected Ring Expansion of an Enantiopure Imidazoline Carbene Ligand [O] . -1

机译：Enaliopure Imidazoline Carbene配体的意外环膨胀

Synthesisof a des-B-Ring BryostatinAnalogue Leads to an Unexpected Ring Expansion of the BryolactoneCore

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