苔藓抑素1的合成研究：通过吡喃环化反应制备C(1)-C(16)片段
Synthetic Studies Toward Bryostatin 1: Preparation of a C(1)-C(16) Fragment by Pyran Annulation.
作者信息
Keck Gary E, Welch Dennie S, Poudel Yam B
机构信息
Department of Chemistry, University of Utah, 315 South 1400 East, RM 2020, Salt Lake City, Utah 84112-0850, USA.
出版信息
Tetrahedron Lett. 2006 Nov 20;47(47):8267-8270. doi: 10.1016/j.tetlet.2006.09.094.
Abstract
An expeditious assembly of a C(1)-C(16) subunit of bryostatin 1 is described. A pyran annulation reaction was utilized to form the B-ring by reaction of a hydroxy-allylsilane with a fully elaborated A-ring subunit. This annulation process proceeded with complete diastereoselectivity and in excellent isolated yield despite the presence of potentially sensitive functionality in the A-ring segment.
摘要
描述了一种快速组装苔藓抑素1的C(1)-C(16)亚基的方法。利用吡喃环化反应，通过羟基烯丙基硅烷与完全合成的A环亚基反应形成B环。尽管A环片段中存在潜在敏感官能团，但该环化过程仍具有完全的非对映选择性且分离产率优异。
相似文献
1
Synthetic Studies Toward Bryostatin 1: Preparation of a C(1)-C(16) Fragment by Pyran Annulation.苔藓抑素1的合成研究：通过吡喃环化反应制备C(1)-C(16)片段
Tetrahedron Lett. 2006 Nov 20;47(47):8267-8270. doi: 10.1016/j.tetlet.2006.09.094.
2
Convergent assembly of highly potent analogues of bryostatin 1 via pyran annulation: bryostatin look-alikes that mimic phorbol ester function.通过吡喃环化反应高效合成苔藓抑素1类似物：模拟佛波酯功能的苔藓抑素类似物
J Am Chem Soc. 2008 May 28;130(21):6660-1. doi: 10.1021/ja8022169. Epub 2008 May 2.
3
Synthetic studies on the bryostatins: preparation of a truncated BC-ring intermediate by pyran annulation.苔藓抑素的合成研究：通过吡喃环化制备截短的BC环中间体。
Org Lett. 2005 May 26;7(11):2149-52. doi: 10.1021/ol050511w.
4
Total synthesis of bryostatin 1.岩大戟内酯 1 的全合成。
J Am Chem Soc. 2011 Feb 2;133(4):744-7. doi: 10.1021/ja110198y. Epub 2010 Dec 22.
5
Sakurai addition and ring annulation of allylsilanes with alpha, beta-unsaturated esters. Experimental results and ab initio theoretical predictions examining allylsilane reactivity.烯丙基硅烷与α,β-不饱和酯的樱井加成反应和环化反应。研究烯丙基硅烷反应活性的实验结果及从头算理论预测。
J Org Chem. 2000 Jun 16;65(12):3666-78. doi: 10.1021/jo991177i.
6
Biological profile of the less lipophilic and synthetically more accessible bryostatin 7 closely resembles that of bryostatin 1.其脂溶性较低、合成更易的 bryostatin 7 的生物学特征与 bryostatin 1 极为相似。
ACS Chem Biol. 2013 Apr 19;8(4):767-77. doi: 10.1021/cb300671s. Epub 2013 Feb 1.
7
Synthesis of arene-functionalized fused heterocyclic scaffolds a regioselective cascade 1,4-conjugate addition/5- annulation strategy.芳烃官能化稠合杂环骨架的合成：一种区域选择性串联1,4-共轭加成/5-环化策略。
Org Biomol Chem. 2023 Nov 29;21(46):9159-9172. doi: 10.1039/d3ob01572f.
8
Replacement of the Bryostatin A- and B-Pyran Rings With Phenyl Rings Leads to Loss of High Affinity Binding With PKC.用苯环取代苔藓抑素A和B的吡喃环会导致与蛋白激酶C的高亲和力结合丧失。
Tetrahedron Lett. 2016 Oct 19;57(42):4749-4753. doi: 10.1016/j.tetlet.2016.09.040.
9
Enantioselective [4 + 2]-annulation of chiral crotylsilanes: application to the synthesis of a C1-C22 fragment of leucascandrolide A.手性巴豆基硅烷的对映选择性[4 + 2]环化反应：在白藜芦醇A的C1-C22片段合成中的应用。
Org Lett. 2003 Oct 16;5(21):3995-8. doi: 10.1021/ol035581m.
10
Synthesis of seco-B-ring bryostatin analogue WN-1 via C-C bond-forming hydrogenation: critical contribution of the B-ring in determining bryostatin-like and phorbol 12-myristate 13-acetate-like properties.通过形成碳-碳键的氢化反应合成开环B环苔藓抑素类似物WN-1：B环在决定苔藓抑素样和佛波醇12-肉豆蔻酸酯13-乙酸酯样性质方面的关键作用。
J Am Chem Soc. 2014 Sep 24;136(38):13209-16. doi: 10.1021/ja507825s. Epub 2014 Sep 10.
引用本文的文献
1
Anticancer Activity of the Marine-Derived Compound Bryostatin 1: Preclinical and Clinical Evaluation.海洋来源化合物苔藓抑素1的抗癌活性：临床前和临床评估
Int J Mol Sci. 2025 Aug 11;26(16):7765. doi: 10.3390/ijms26167765.
2
Prins cyclization-mediated stereoselective synthesis of tetrahydropyrans and dihydropyrans: an inspection of twenty years.普林斯环化介导的四氢吡喃和二氢吡喃的立体选择性合成：二十年审视
Beilstein J Org Chem. 2021 Apr 29;17:932-963. doi: 10.3762/bjoc.17.77. eCollection 2021.
3
Synthesis and Biological Evaluation of Fluorescent Bryostatin Analogues.荧光苔藓抑素类似物的合成与生物评价。
Chembiochem. 2018 Apr 16;19(8):877-889. doi: 10.1002/cbic.201700655. Epub 2018 Mar 25.
4
Synthesis of a des-B-ring bryostatin analogue leads to an unexpected ring expansion of the bryolactone core.一种去-B环苔藓抑素类似物的合成导致苔藓内酯核心出现意外的环扩展。
J Am Chem Soc. 2014 Sep 24;136(38):13202-8. doi: 10.1021/ja5078188. Epub 2014 Sep 10.
5
Mechanistic and computational studies of exocyclic stereocontrol in the synthesis of bryostatin-like cis-2,6-disubstituted 4-alkylidenetetrahydropyrans by Prins cyclization.通过普林斯环化反应合成类似苔藓抑素的顺式-2,6-二取代 4-亚烷基四氢吡喃时的非环立体控制的机理和计算研究。
J Org Chem. 2013 Jan 4;78(1):104-15. doi: 10.1021/jo301953h. Epub 2012 Nov 7.
6
Translating Nature's Library: The Bryostatins and Function-Oriented Synthesis.解读自然文库：苔藓抑素与功能导向合成
Isr J Chem. 2011 Apr 1;51(3-4):453-472. doi: 10.1002/ijch.201100020. Epub 2011 Mar 24.
7
Total synthesis of bryostatin 7 via C-C bond-forming hydrogenation.通过 C-C 键形成氢化反应全合成海鞘素 7。
J Am Chem Soc. 2011 Sep 7;133(35):13876-9. doi: 10.1021/ja205673e. Epub 2011 Aug 11.
8
Total synthesis of bryostatin 1.岩大戟内酯 1 的全合成。
J Am Chem Soc. 2011 Feb 2;133(4):744-7. doi: 10.1021/ja110198y. Epub 2010 Dec 22.
9
Molecular modeling, total synthesis, and biological evaluations of C9-deoxy bryostatin 1.C9-脱氧苔藓抑素1的分子模拟、全合成及生物学评价
Angew Chem Int Ed Engl. 2010 Jun 21;49(27):4580-4. doi: 10.1002/anie.201001200.
10
Concise synthesis of the bryostatin A-ring via consecutive C-C bond forming transfer hydrogenations.通过连续的碳-碳键形成转移氢化反应简洁合成苔藓抑素A环。
Org Lett. 2009 Jul 16;11(14):3108-11. doi: 10.1021/ol901096d.
本文引用的文献
1
Synthetic studies toward the bryostatins: a substrate-controlled approach to the A-ring.苔藓抑素的合成研究：A环的底物控制合成方法。
Org Lett. 2006 Aug 17;8(17):3667-70. doi: 10.1021/ol061173h.
2
Targeting the cell cycle: a new approach to cancer therapy.靶向细胞周期：癌症治疗的新方法。
J Clin Oncol. 2005 Dec 20;23(36):9408-21. doi: 10.1200/JCO.2005.01.5594.
3
Protein synthesis required for long-term memory is induced by PKC activation on days before associative learning.长期记忆所需的蛋白质合成是在联想学习前几天由蛋白激酶C激活诱导产生的。
Proc Natl Acad Sci U S A. 2005 Nov 8;102(45):16432-7. doi: 10.1073/pnas.0508001102. Epub 2005 Oct 28.
4
Protein kinase C (PKC) family in cancer progression.蛋白激酶C（PKC）家族在癌症进展中的作用
Cancer Lett. 2006 Apr 8;235(1):1-10. doi: 10.1016/j.canlet.2005.03.033.
5
Synthetic studies on the bryostatins: synthetic routes to analogues containing the tricyclic macrolactone core.苔藓抑素的合成研究：含三环大环内酯核心类似物的合成路线
Org Lett. 2005 May 26;7(11):2153-6. doi: 10.1021/ol050512o.
6
Synthetic studies on the bryostatins: preparation of a truncated BC-ring intermediate by pyran annulation.苔藓抑素的合成研究：通过吡喃环化制备截短的BC环中间体。
Org Lett. 2005 May 26;7(11):2149-52. doi: 10.1021/ol050511w.
7
Dual effects of bryostatin-1 on spatial memory and depression.苔藓抑素-1对空间记忆和抑郁的双重作用。
Eur J Pharmacol. 2005 Apr 4;512(1):43-51. doi: 10.1016/j.ejphar.2005.02.028.
8
Enantio- and diastereoselective additions to aldehydes using the bifunctional reagent 2-(chloromethyl)-3-(tributylstannyl)propene: application to a synthesis of the C16-C27 segment of bryostatin 1.使用双功能试剂2-(氯甲基)-3-(三丁基锡烷基)丙烯对醛进行对映选择性和非对映选择性加成：应用于苔藓抑素1的C16 - C27片段的合成
J Org Chem. 2005 Apr 1;70(7):2543-50. doi: 10.1021/jo048308m.
9
Synthesis of the bryostatin 1 northern hemisphere (C1-C16) via desymmetrization by ketalization/ring-closing metathesis.通过缩酮化/闭环复分解去对称化合成苔藓抑素1北半球片段（C1-C16）。
Org Lett. 2004 Oct 28;6(22):4045-8. doi: 10.1021/ol0483044.
10
Marine natural products and related compounds in clinical and advanced preclinical trials.处于临床和临床前高级试验阶段的海洋天然产物及相关化合物。
J Nat Prod. 2004 Aug;67(8):1216-38. doi: 10.1021/np040031y.
Zotero 插件