(-)-伊鲁替尼 B 的全合成及通过化学转化为 (+)-伊鲁替尼 A（石蒜裂碱）的结构确证。
Total synthesis of (-)-irciniastatin B and structural confirmation via chemical conversion to (+)-irciniastatin A (psymberin).
机构信息
Department of Chemistry, Laboratory for Research on the Structure of Matter and Monell Chemical Senses Center, University of Pennsylvania, Philadelphia, Pennsylvania 19104, USA.
出版信息
Org Lett. 2012 Sep 7;14(17):4350-3. doi: 10.1021/ol301783p. Epub 2012 Aug 14.
Abstract
The total synthesis and structural confirmation of the marine sponge cytotoxin (-)-irciniastatin B has been achieved via a unified strategy employing a late-stage, selective deprotection/oxidation sequence that provides access to both (+)-irciniastatin A (psymberin) and (-)-irciniastatin B.
摘要
通过采用晚期选择性保护/氧化序列的统一策略，实现了海洋海绵细胞毒素 (-)-irciniastatin B 的全合成和结构确证，该策略可同时获得 (+)-irciniastatin A（psymberin）和 (-)-irciniastatin B。
相似文献
1
Total synthesis of (-)-irciniastatin B and structural confirmation via chemical conversion to (+)-irciniastatin A (psymberin).(-)-伊鲁替尼 B 的全合成及通过化学转化为 (+)-伊鲁替尼 A（石蒜裂碱）的结构确证。
Org Lett. 2012 Sep 7;14(17):4350-3. doi: 10.1021/ol301783p. Epub 2012 Aug 14.
2
Total synthesis of (+)-psymberin (irciniastatin A): catalytic reagent control as the strategic cornerstone.（+）- 苔藓虫素（海棉他汀A）的全合成：以催化试剂控制作为战略基石
Org Lett. 2008 Dec 18;10(24):5625-8. doi: 10.1021/ol802466t.
3
Total synthesis of (+)-irciniastatin A (a.k.a. psymberin) and (-)-irciniastatin B.(+)- 伊鲁替尼 A（又名 psymberin）和 (-)- 伊鲁替尼 B 的全合成。
J Org Chem. 2013 May 3;78(9):4278-96. doi: 10.1021/jo400260m. Epub 2013 Apr 12.
4
Total Synthesis and Biological Evaluation of Irciniastatin A (a.k.a. Psymberin) and Irciniastatin B.刺胞酸A（又名苔藓抑素）和刺胞酸B的全合成及生物学评价
J Org Chem. 2015 Dec 18;80(24):12333-50. doi: 10.1021/acs.joc.5b02256. Epub 2015 Nov 16.
5
Synthesis and complete stereochemical assignment of psymberin/irciniastatin A.苔藓虫素/刺胞酸A的合成及完整立体化学归属
J Am Chem Soc. 2005 Aug 17;127(32):11254-5. doi: 10.1021/ja0537068.
6
The discovery of potent antitumor agent C11-deoxypsymberin/irciniastatin A: total synthesis and biology of advanced psymberin analogs.强效抗肿瘤药物C11-脱氧苔藓抑素/刺参抑素A的发现：苔藓抑素类似物的全合成及生物学研究
Org Lett. 2009 Feb 19;11(4):867-70. doi: 10.1021/ol802772s.
7
Design, Synthesis, and Evaluation of Irciniastatin Analogues: Simplification of the Tetrahydropyran Core and the C(11) Substituents.艾氏海绵他汀类似物的设计、合成与评价：四氢吡喃核心结构及C(11)取代基的简化
J Org Chem. 2016 Mar 4;81(5):1930-42. doi: 10.1021/acs.joc.5b02771. Epub 2016 Feb 16.
8
Total synthesis of irciniastatin A (Psymberin).刺参他汀A（苔藓虫素）的全合成。
Org Lett. 2009 Sep 3;11(17):3990-3. doi: 10.1021/ol901655e.
9
Fluorescent analogs of the marine natural product psammaplin A: synthesis and biological activity.海洋天然产物沙玛平 A 的荧光类似物：合成与生物活性。
Org Biomol Chem. 2012 Sep 21;10(35):7120-33. doi: 10.1039/c2ob25909e. Epub 2012 Aug 7.
10
Total synthesis and cytotoxic activity of stellatin.斯泰拉汀的全合成及细胞毒性活性
J Asian Nat Prod Res. 2011 Feb;13(2):97-104. doi: 10.1080/10286020.2010.544654.
引用本文的文献
1
Design, Synthesis, and Evaluation of Irciniastatin Analogues: Simplification of the Tetrahydropyran Core and the C(11) Substituents.艾氏海绵他汀类似物的设计、合成与评价：四氢吡喃核心结构及C(11)取代基的简化
J Org Chem. 2016 Mar 4;81(5):1930-42. doi: 10.1021/acs.joc.5b02771. Epub 2016 Feb 16.
2
Asymmetric Synthesis of the C1-C6 Portion of the Psymberin Using an Evans Chiral Auxiliary.使用伊文斯手性助剂不对称合成苔藓抑素的C1-C6部分。
Tetrahedron Lett. 2013 Oct 9;54(41):5555-5567. doi: 10.1016/j.tetlet.2013.05.153.
3
Total synthesis of (+)-irciniastatin A (a.k.a. psymberin) and (-)-irciniastatin B.(+)- 伊鲁替尼 A（又名 psymberin）和 (-)- 伊鲁替尼 B 的全合成。
J Org Chem. 2013 May 3;78(9):4278-96. doi: 10.1021/jo400260m. Epub 2013 Apr 12.
本文引用的文献
1
Stereoselective synthesis of 2,6-trans-tetrahydropyran via primary diamine-catalyzed oxa-conjugate addition reaction of α,β-unsaturated ketone: total synthesis of psymberin.通过伯胺催化的α,β-不饱和酮的氧杂共轭加成反应立体选择性合成 2,6-反式四氢吡喃：psymberin 的全合成。
Org Lett. 2011 Nov 4;13(21):5816-9. doi: 10.1021/ol2024289. Epub 2011 Oct 11.
2
Total synthesis and biological evaluation of pederin, psymberin, and highly potent analogs.总合成及对异戊烯基菲并呋喃喹啉、扁柏双黄酮及高活性类似物的生物评价。
J Am Chem Soc. 2011 Oct 19;133(41):16668-79. doi: 10.1021/ja207331m. Epub 2011 Sep 22.
3
Irciniastatin A induces JNK activation that is involved in caspase-8-dependent apoptosis via the mitochondrial pathway.伊鲁替尼诱导 JNK 激活，通过线粒体途径参与 caspase-8 依赖性细胞凋亡。
Toxicol Lett. 2010 Dec 15;199(3):341-6. doi: 10.1016/j.toxlet.2010.09.017.
4
Total Synthesis of (+)-Papulacandin D.（+）-丘疹霉素D的全合成
Tetrahedron. 2010 Jun 26;66(26):4745-4759. doi: 10.1016/j.tet.2010.03.093.
5
Syntheses and biological evaluation of irciniastatin A and the C1-C2 alkyne analogue.irciniastatin A 及其 C1-C2 炔烃类似物的合成与生物评价。
Org Lett. 2010 Mar 5;12(5):1040-3. doi: 10.1021/ol1000389.
6
Total synthesis of irciniastatin A (Psymberin).刺参他汀A（苔藓虫素）的全合成。
Org Lett. 2009 Sep 3;11(17):3990-3. doi: 10.1021/ol901655e.
7
The discovery of potent antitumor agent C11-deoxypsymberin/irciniastatin A: total synthesis and biology of advanced psymberin analogs.强效抗肿瘤药物C11-脱氧苔藓抑素/刺参抑素A的发现：苔藓抑素类似物的全合成及生物学研究
Org Lett. 2009 Feb 19;11(4):867-70. doi: 10.1021/ol802772s.
8
Total synthesis of (+)-psymberin (irciniastatin A): catalytic reagent control as the strategic cornerstone.（+）- 苔藓虫素（海棉他汀A）的全合成：以催化试剂控制作为战略基石
Org Lett. 2008 Dec 18;10(24):5625-8. doi: 10.1021/ol802466t.
9
The total synthesis of psymberin.苔藓虫素的全合成。
Org Lett. 2007 Jun 21;9(13):2597-600. doi: 10.1021/ol071068n. Epub 2007 May 25.
10
Synthesis and complete stereochemical assignment of psymberin/irciniastatin A.苔藓虫素/刺胞酸A的合成及完整立体化学归属
J Am Chem Soc. 2005 Aug 17;127(32):11254-5. doi: 10.1021/ja0537068.
Zotero 插件