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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。

Synthetic studies on the bryostatins: preparation of a truncated BC-ring intermediate by pyran annulation.

作者信息

Keck Gary E, Truong Anh P

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

Org Lett. 2005 May 26;7(11):2149-52. doi: 10.1021/ol050511w.

DOI:10.1021/ol050511w
PMID:15901156
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC1480406/
Abstract

[reaction: see text]. A synthesis of a potential BC-ring subunit (C9-C27) for bryostatin 1, a remarkably potent anticancer agent, has been developed in 16 steps and 18% overall yield. The key features of this route include a BITIP-catalyzed asymmetric allylation reaction, chelation-controlled allylations, a hydroformylation reaction, and a pyran annulation reaction.

摘要

[反应:见正文]。已开发出一种用于苔藓抑素1(一种极具潜力的抗癌药物)的潜在BC环亚基(C9 - C27)的合成方法,该方法共16步,总产率为18%。此路线的关键特征包括BITIP催化的不对称烯丙基化反应、螯合控制的烯丙基化反应、氢甲酰化反应和吡喃环化反应。

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本文引用的文献

1
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.
2
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.
3
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.
4
Concise formal synthesis of the bryostatin southern hemisphere (C17-C27).苔藓抑素南半球部分(C17 - C27)的简洁形式合成。
J Org Chem. 2004 Jun 25;69(13):4534-7. doi: 10.1021/jo0495081.
5
New, abridged pathway to Masamune's "southern hemisphere" intermediate for the total synthesis of bryostatin 7.用于苔藓抑素7全合成的通向正宗“南半球”中间体的新的简化途径。
Org Lett. 2003 Feb 20;5(4):503-5. doi: 10.1021/ol027393m.
6
Synthesis of a simplified bryostatin C-ring analogue that binds to the CRD2 of human PKC-alpha and construction of a novel BC-analogue by an unusual Julia olefination process.
Org Lett. 2003 Feb 20;5(4):499-502. doi: 10.1021/ol027392u.
7
The practical synthesis of a novel and highly potent analogue of bryostatin.苔藓抑素一种新型高效类似物的实际合成。
J Am Chem Soc. 2002 Nov 20;124(46):13648-9. doi: 10.1021/ja027509+.
8
The chemistry and biology of the bryostatin antitumour macrolides.苔藓抑素抗肿瘤大环内酯类化合物的化学与生物学
Nat Prod Rep. 2002 Aug;19(4):413-53. doi: 10.1039/b009211h.
9
Pyran annulation: asymmetric synthesis of 2,6-disubstituted-4-methylene tetrahydropyrans.吡喃环化反应:2,6-二取代-4-亚甲基四氢吡喃的不对称合成
Org Lett. 2002 Apr 4;4(7):1189-92. doi: 10.1021/ol025645d.
10
Chemistry and clinical biology of the bryostatins.
Bioorg Med Chem. 2000 Aug;8(8):1841-60. doi: 10.1016/s0968-0896(00)00150-4.