短裸甲藻毒素A的全合成。
Total synthesis of brevetoxin A.
作者信息
Crimmins Michael T, Zuccarello J Lucas, Ellis J Michael, McDougall Patrick J, Haile Pamela A, Parrish Jonathan D, Emmitte Kyle A
机构信息
Department of Chemistry, Venable and Kenan Laboratories of Chemistry, University of North Carolina at Chapel Hill, Chapel Hill, North Carolina 27599-3290, USA.
出版信息
Org Lett. 2009 Jan 15;11(2):489-92. doi: 10.1021/ol802710u.
Abstract
A total synthesis of brevetoxin A is reported. Two tetracyclic coupling partners, prepared from previously reported advanced fragments, were effectively united via a Horner-Wittig olefination. The resulting octacycle was progressed to substrates that were explored for reductive etherification, the success of which led to a penultimate tetraol intermediate. The tetraol was converted to the natural product through an expeditious selective oxidative process followed by methylenation.
摘要
报道了短裸甲藻毒素A的全合成。由先前报道的高级片段制备的两个四环偶联伙伴通过霍纳尔-维蒂希烯烃化反应有效地结合在一起。所得的八环化合物进一步转化为用于还原醚化反应研究的底物，该反应的成功得到了一个倒数第二个四醇中间体。通过快速的选择性氧化过程，然后进行亚甲基化反应，将四醇转化为天然产物。
相似文献
1
Total synthesis of brevetoxin A.短裸甲藻毒素A的全合成。
Org Lett. 2009 Jan 15;11(2):489-92. doi: 10.1021/ol802710u.
2
Enantioselective total synthesis of brevetoxin A: convergent coupling strategy and completion.短裸甲藻毒素A的对映选择性全合成：汇聚偶联策略与完成
Chemistry. 2009 Sep 14;15(36):9235-44. doi: 10.1002/chem.200900777.
3
Convergent, stereoselective synthesis of the GHIJ fragment of brevetoxin A.短裸甲藻毒素A的GHIJ片段的汇聚式、立体选择性合成
Org Lett. 2006 Jan 5;8(1):159-62. doi: 10.1021/ol0526625.
4
A convergent coupling strategy for the formation of polycyclic ethers: stereoselective synthesis of the BCDE fragment of brevetoxin A.一种用于形成多环醚的汇聚偶联策略：短裸甲藻毒素A的BCDE片段的立体选择性合成
Org Lett. 2005 Sep 1;7(18):4033-6. doi: 10.1021/ol051543m.
5
Synthesis of the Framework of Tamulamides A and B.塔玛兰酰胺 A 和 B 的骨架合成。
Org Lett. 2019 Oct 4;21(19):8027-8030. doi: 10.1021/acs.orglett.9b03015. Epub 2019 Sep 16.
6
A total synthesis trilogy: calicheamicin γ1(I), Taxol®, and brevetoxin A.一个全合成三部曲：加利车霉素 γ1（I）、紫杉醇和布雷菲德菌素 A。
Chem Rec. 2012 Aug;12(4):407-41. doi: 10.1002/tcr.201200005. Epub 2012 Jun 18.
7
Synthesis of the ABCDEFG ring system of maitotoxin.麦角酸毒素 ABCDEFG 环系的合成。
J Am Chem Soc. 2010 May 19;132(19):6855-61. doi: 10.1021/ja102260q.
8
Synthesis of the bis-tetrahydropyran core of amphidinol 3.合成 Amphidinol 3 的双四氢吡喃核心。
Org Lett. 2010 Sep 3;12(17):3890-3. doi: 10.1021/ol1015898.
9
Total synthesis of brevetoxin B.短裸甲藻毒素B的全合成。
J Am Chem Soc. 2005 Jun 29;127(25):9246-50. doi: 10.1021/ja051171c.
10
Enantioselective total synthesis of brevetoxin A: unified strategy for the B, E, G, and J subunits.短裸甲藻毒素A的对映选择性全合成：B、E、G和J亚基的统一策略。
Chemistry. 2009 Sep 14;15(36):9223-34. doi: 10.1002/chem.200900776.
引用本文的文献
1
Organic synthesis: the art and science of replicating the molecules of living nature and creating others like them in the laboratory.有机合成：在实验室中复制生命自然界的分子并创造类似分子的艺术与科学。
Proc Math Phys Eng Sci. 2014 Mar 8;470(2163):20130690. doi: 10.1098/rspa.2013.0690.
2
Constructing molecular complexity and diversity: total synthesis of natural products of biological and medicinal importance.构建分子复杂性和多样性：生物和医学重要性天然产物的全合成。
Chem Soc Rev. 2012 Aug 7;41(15):5185-238. doi: 10.1039/c2cs35116a. Epub 2012 Jun 28.
3
Maitotoxin: An Inspiration for Synthesis.maitotoxin：合成的灵感来源。
Isr J Chem. 2011 Apr;51(3-4):359-377. doi: 10.1002/ijch.201100003.
4
Review of Florida Red Tide and Human Health Effects.佛罗里达赤潮及其对人类健康影响的综述。
Harmful Algae. 2011 Jan 1;10(2):224-233. doi: 10.1016/j.hal.2010.08.006.
5
Development of novel drugs from marine surface associated microorganisms.海洋表面相关微生物新型药物的开发。
Mar Drugs. 2010 Mar 1;8(3):438-59. doi: 10.3390/md8030438.
6
The development of endo-selective epoxide-opening cascades in water.在水中发展的内选择性环氧化物开环级联反应。
Chem Soc Rev. 2009 Nov;38(11):3175-92. doi: 10.1039/b816697h. Epub 2009 Sep 16.
7
Enantioselective total synthesis of brevetoxin A: convergent coupling strategy and completion.短裸甲藻毒素A的对映选择性全合成：汇聚偶联策略与完成
Chemistry. 2009 Sep 14;15(36):9235-44. doi: 10.1002/chem.200900777.
8
Enantioselective total synthesis of brevetoxin A: unified strategy for the B, E, G, and J subunits.短裸甲藻毒素A的对映选择性全合成：B、E、G和J亚基的统一策略。
Chemistry. 2009 Sep 14;15(36):9223-34. doi: 10.1002/chem.200900776.
本文引用的文献
1
Structure of brevetoxin A (GB-1 toxin), the most potent toxin in the Florida red tide organism Gymnodinium breve (Ptychodiscus brevis).短裸甲藻毒素A（GB-1毒素）的结构，它是佛罗里达赤潮生物短裸甲藻（短角藻）中最具毒性的毒素。
J Am Chem Soc. 1986 Feb 1;108(3):514-5. doi: 10.1021/ja00263a031.
2
Environmental exposures to Florida red tides: Effects on emergency room respiratory diagnoses admissions.佛罗里达赤潮对环境的暴露：对急诊室呼吸道诊断入院病例的影响。
Harmful Algae. 2006 Oct 1;5(5):526-533. doi: 10.1016/j.hal.2005.09.004.
3
Synthesis, modeling, and biological evaluation of analogues of the semisynthetic brevetoxin antagonist beta-naphthoyl-brevetoxin.半合成短裸甲藻毒素拮抗剂β-萘甲酰基短裸甲藻毒素类似物的合成、建模及生物学评价
Chembiochem. 2007 Dec 17;8(18):2233-9. doi: 10.1002/cbic.200700317.
4
Recent advances in the synthesis of marine polycyclic ether natural products.海洋多环醚天然产物合成的最新进展。
Curr Opin Drug Discov Devel. 2007 Nov;10(6):784-806.
5
Brevetoxins, like ciguatoxins, are potent ichthyotoxic neurotoxins that accumulate in fish.短裸甲藻毒素与雪卡毒素一样，是在鱼类体内积累的强效鱼毒性神经毒素。
Toxicon. 2007 Oct;50(5):707-23. doi: 10.1016/j.toxicon.2007.06.005. Epub 2007 Jun 26.
6
Improved synthesis of the ABCDE fragment of brevetoxin A.短裸甲藻毒素A的ABCDE片段的合成改进
Org Lett. 2006 Aug 31;8(18):4079-82. doi: 10.1021/ol0615782.
7
Convergent, stereoselective synthesis of the GHIJ fragment of brevetoxin A.短裸甲藻毒素A的GHIJ片段的汇聚式、立体选择性合成
Org Lett. 2006 Jan 5;8(1):159-62. doi: 10.1021/ol0526625.
8
Convergent strategies for syntheses of trans-fused polycyclic ethers.反式稠合多环醚合成的汇聚策略。
Chem Rev. 2005 Dec;105(12):4379-405. doi: 10.1021/cr0406108.
9
Total synthesis of marine polycyclic ethers.海洋多环醚的全合成。
Chem Rev. 2005 Dec;105(12):4314-47. doi: 10.1021/cr040627q.
10
A convergent coupling strategy for the formation of polycyclic ethers: stereoselective synthesis of the BCDE fragment of brevetoxin A.一种用于形成多环醚的汇聚偶联策略：短裸甲藻毒素A的BCDE片段的立体选择性合成
Org Lett. 2005 Sep 1;7(18):4033-6. doi: 10.1021/ol051543m.
Zotero 插件