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Literature DB >> 20148525

Total synthesis of lycogarubin C and lycogalic acid.

Abstract

Two complementary concise total syntheses of lycogarubin C (1) and lycogalic acid (2, aka chromopyrrolic acid) are detailed utilizing a 1,2,4,5-tetrazine --> 1,2-diazine --> pyrrole Diels-Alder strategy and enlisting acetylenic dienophiles.

Entities: Chemical Species

Mesh：

Substances：

Year: 2010 PMID： 20148525 PMCID： PMC2832087 DOI： 10.1021/ol100146b

Source DB: PubMed Journal: Org Lett ISSN： 1523-7052 Impact factor: 6.005

21 in total

Review 1. Isolation and synthesis of biologically active carbazole alkaloids.

Authors: Hans-Joachim Knölker; Kethiri R Reddy
Journal: Chem Rev Date: 2002-11 Impact factor: 60.622

2. Total synthesis of anhydrolycorinone utilizing sequential intramolecular Diels-Alder reactions of a 1,3,4-oxadiazole.

Authors: Scott E Wolkenberg; Dale L Boger
Journal: J Org Chem Date: 2002-10-18 Impact factor: 4.354

3. Staurosporine and rebeccamycin aglycones are assembled by the oxidative action of StaP, StaC, and RebC on chromopyrrolic acid.

Authors: Annaleise R Howard-Jones; Christopher T Walsh
Journal: J Am Chem Soc Date: 2006-09-20 Impact factor: 15.419

4. Asymmetric total synthesis of ent-(-)-roseophilin: assignment of absolute configuration.

Authors: D L Boger; J Hong
Journal: J Am Chem Soc Date: 2001-09-05 Impact factor: 15.419

5. Total synthesis of ningalin B utilizing a heterocyclic azadiene Diels-Alder reaction and discovery of a new class of potent multidrug resistant (MDR) reversal agents.

Authors: D L Boger; D R Soenen; C W Boyce; M P Hedrick; Q Jin
Journal: J Org Chem Date: 2000-04-21 Impact factor: 4.354

6. Total synthesis of Amaryllidaceae alkaloids utilizing sequential intramolecular heterocyclic azadiene Diels-Alder reactions of an unsymmetrical 1,2,4,5-tetrazine.

Authors: D L Boger; S E Wolkenberg
Journal: J Org Chem Date: 2000-12-29 Impact factor: 4.354

7. Total synthesis of vinblastine, vincristine, related natural products, and key structural analogues.

Authors: Hayato Ishikawa; David A Colby; Shigeki Seto; Porino Va; Annie Tam; Hiroyuki Kakei; Thomas J Rayl; Inkyu Hwang; Dale L Boger
Journal: J Am Chem Soc Date: 2009-04-08 Impact factor: 15.419

8. Theoretical and experimental studies of the conversion of chromopyrrolic acid to an antitumor derivative by cytochrome P450 StaP: the catalytic role of water molecules.

Authors: Yong Wang; Hui Chen; Masatomo Makino; Yoshitsugu Shiro; Shingo Nagano; Shumpei Asamizu; Hiroyasu Onaka; Sason Shaik
Journal: J Am Chem Soc Date: 2009-05-20 Impact factor: 15.419

9. Production of chromopyrrolic acid by coexpression of inkOD in a heterologous host Streptomyces albus.

Authors: Choong-Sik Chae; Jin-Soo Park; Soon-Chun Chung; Tae-Im Kim; So-Hyoung Lee; Kyung-Mi Yoon; Jongheon Shin; Ki-Bong Oh
Journal: Bioorg Med Chem Lett Date: 2009-02-11 Impact factor: 2.823

10. Crystal structures and catalytic mechanism of cytochrome P450 StaP that produces the indolocarbazole skeleton.

Authors: Masatomo Makino; Hiroshi Sugimoto; Yoshitsugu Shiro; Shumpei Asamizu; Hiroyasu Onaka; Shingo Nagano
Journal: Proc Natl Acad Sci U S A Date: 2007-07-02 Impact factor: 11.205

11 in total

1. Total synthesis of dihydrolysergic acid and dihydrolysergol: development of a divergent synthetic strategy applicable to rapid assembly of D-ring analogs.

Authors: Kiyoun Lee; Yam B Poudel; Christopher M Glinkerman; Dale L Boger
Journal: Tetrahedron Date: 2015-09-02 Impact factor: 2.457

2. Synthesis, Characterization, and Rapid Cycloadditions of 5-Nitro-1,2,3-triazine.

Authors: Christopher M Glinkerman; Dale L Boger
Journal: Org Lett Date: 2018-04-16 Impact factor: 6.005

3. Cycloadditions of 1,2,3-Triazines Bearing C5-Electron Donating Substituents: Robust Pyrimidine Synthesis.

Authors: Christopher M Glinkerman; Dale L Boger
Journal: Org Lett Date: 2015-07-14 Impact factor: 6.005

4. Inverse electron demand Diels-Alder reactions of 1,2,3-triazines: pronounced substituent effects on reactivity and cycloaddition scope.

Authors: Erin D Anderson; Dale L Boger
Journal: J Am Chem Soc Date: 2011-07-19 Impact factor: 15.419

5. The application of formyl group activation of bromopyrrole esters to formal syntheses of lycogarubin C, permethyl storniamide A and lamellarin G trimethyl ether.

Authors: John T Gupton; Nakul Telang; Jon Patteson; Kristin Lescalleet; Scott Yeudall; John Sobieski; Andrew Harrison; Will Curry
Journal: Tetrahedron Date: 2014-12-30 Impact factor: 2.457

6. Scope of the inverse electron demand Diels-Alder reactions of 1,2,3-triazine.

Authors: Erin D Anderson; Dale L Boger
Journal: Org Lett Date: 2011-04-13 Impact factor: 6.005

7. Direct Synthesis of β-Aminoenals through Reaction of 1,2,3-Triazine with Secondary Amines.

Authors: Ryan E Quiñones; Christopher M Glinkerman; Kaicheng Zhu; Dale L Boger
Journal: Org Lett Date: 2017-06-28 Impact factor: 6.005

Review 8. Inverse Electron Demand Diels-Alder Reactions of Heterocyclic Azadienes, 1-Aza-1,3-Butadienes, Cyclopropenone Ketals, and Related Systems. A Retrospective.

Authors: Jiajun Zhang; Vyom Shukla; Dale L Boger
Journal: J Org Chem Date: 2019-05-23 Impact factor: 4.354

9. Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles.

Authors: John T Gupton; Nakul Telang; Dominic F Gazzo; Peter J Barelli; Kristin E Lescalleet; Jonathan W Fagan; Brandon J Mills; Kara L Finzel; Rene P F Kanters; Kyle R Crocker; Sean T Dudek; Corinne M Lariviere; Stanton Q Smith; Kartik M Keertikar
Journal: Tetrahedron Date: 2013-07-22 Impact factor: 2.457

10. Cycloadditions of noncomplementary substituted 1,2,3-triazines.

Authors: Erin D Anderson; Adam S Duerfeldt; Kaicheng Zhu; Christopher M Glinkerman; Dale L Boger
Journal: Org Lett Date: 2014-09-15 Impact factor: 6.005