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Literature DB >> 22860227

Total synthesis of diazonamide A.

Robert R Knowles¹, Joseph Carpenter, Simon B Blakey, Akio Kayano, Ian K Mangion, Christopher J Sinz, David W C Macmillan.

Abstract

A total synthesis of the marine natural product diazonamide A (1) has been accomplished. This work features a highly stereoselective synthesis of the C(10) quaternary center and the central furanoindoline core enabled by an iminium-catalyzed alkylation-cyclization cascade. Additionally, a magnesium-mediated intramolecular macroaldolization and a palladium-catalyzed tandem borylation/annulation were developed to enable the closure of the two 12-membered macrocycles of diazonamide A. This synthesis involves 20 steps in its longest linear sequence and proceeds in 1.8% overall yield.

Entities: Chemical Disease Gene Species

Year: 2010 PMID： 22860227 PMCID： PMC3408608 DOI： 10.1039/C0SC00577K

Source DB: PubMed Journal: Chem Sci ISSN： 2041-6520 Impact factor: 9.825

18 in total

1. The second total synthesis of diazonamide A.

Authors: K C Nicolaou; Paraselli Bheema Rao; Junliang Hao; Mali Venkat Reddy; Gerasimos Rassias; Xianhai Huang; David Y-K Chen; Scott A Snyder
Journal: Angew Chem Int Ed Engl Date: 2003-04-17 Impact factor: 15.336

2. Total Synthesis of Nominal Diazonamides-Part 2: On the True Structure and Origin of Natural Isolates Funding provided by the NIH (RO1-GM60591), the NSF (CAREER 9984282), the Howard Hughes Medical Institute (junior faculty support), the Robert A. Welch Foundation, and the Advanced Research Program of the Texas Higher Education Coordinating Board. We are grateful to Professor Michael Roth for his time, insight, and advice.

Authors: Jing Li; Anthony W. G. Burgett; Lothar Esser; Carlos Amezcua; Patrick G. Harran
Journal: Angew Chem Int Ed Engl Date: 2001-12-17 Impact factor: 15.336

3. A concise and flexible total synthesis of (-)-diazonamide A.

Authors: Anthony W G Burgett; Qingyi Li; Qi Wei; Patrick G Harran
Journal: Angew Chem Int Ed Engl Date: 2003-10-20 Impact factor: 15.336

4. Chemistry and biology of diazonamide A: second total synthesis and biological investigations.

Authors: K C Nicolaou; Junliang Hao; Mali V Reddy; Paraselli Bheema Rao; Gerasimos Rassias; Scott A Snyder; Xianhai Huang; David Y-K Chen; William E Brenzovich; Nicolas Giuseppone; Aurora O'Brate; Paraskevi Giannakakou
Journal: J Am Chem Soc Date: 2004-10-13 Impact factor: 15.419

5. Chemistry and biology of diazonamide A: first total synthesis and confirmation of the true structure.

Authors: K C Nicolaou; David Y-K Chen; Xianhai Huang; Taotao Ling; Marco Bella; Scott A Snyder
Journal: J Am Chem Soc Date: 2004-10-13 Impact factor: 15.419

6. Total Synthesis of Nominal Diazonamides-Part 1: Convergent Preparation of the Structure Proposed for (-)-Diazonamide A Funding provided by the NIH (RO1-GM60591), the NSF (CAREER 9984282), the Howard Hughes Medical Institute (junior faculty support), the Robert A. Welch Foundation, and the Advanced Research Program of the Texas Higher Education Coordinating Board.

Authors: Jing Li; Susan Jeong; Lothar Esser; Patrick G. Harran
Journal: Angew Chem Int Ed Engl Date: 2001-12-17 Impact factor: 15.336

7. A concise formal synthesis of diazonamide A by the stereoselective construction of the C10 quaternary center.

Authors: Cheng-Kang Mai; Matthew F Sammons; Tarek Sammakia
Journal: Angew Chem Int Ed Engl Date: 2010-03-22 Impact factor: 15.336

8. Diazonamide toxins reveal an unexpected function for ornithine delta-amino transferase in mitotic cell division.

Authors: Gelin Wang; Libin Shang; Anthony W G Burgett; Patrick G Harran; Xiaodong Wang
Journal: Proc Natl Acad Sci U S A Date: 2007-02-07 Impact factor: 11.205

9. Diazonamide A and a synthetic structural analog: disruptive effects on mitosis and cellular microtubules and analysis of their interactions with tubulin.

Authors: Zobeida Cruz-Monserrate; Hélène C Vervoort; Ruoli Bai; David J Newman; Stephen B Howell; Gerrit Los; Jeffrey T Mullaney; Michael D Williams; George R Pettit; William Fenical; Ernest Hamel
Journal: Mol Pharmacol Date: 2003-06 Impact factor: 4.436

10. Nine-step enantioselective total synthesis of (+)-minfiensine.

Authors: Spencer B Jones; Bryon Simmons; David W C MacMillan
Journal: J Am Chem Soc Date: 2009-09-30 Impact factor: 15.419

10 in total

Review 1. Constructing molecular complexity and diversity: total synthesis of natural products of biological and medicinal importance.

Authors: K C Nicolaou; Christopher R H Hale; Christian Nilewski; Heraklidia A Ioannidou
Journal: Chem Soc Rev Date: 2012-06-28 Impact factor: 54.564

Review 2. Natural Products in the "Marketplace": Interfacing Synthesis and Biology.

Authors: Benjamin J Huffman; Ryan A Shenvi
Journal: J Am Chem Soc Date: 2019-02-13 Impact factor: 15.419

3. Thionium ion initiated medium-sized ring formation: the total synthesis of asteriscunolide D.

Authors: Barry M Trost; Aaron C Burns; Mark J Bartlett; Thomas Tautz; Andrew H Weiss
Journal: J Am Chem Soc Date: 2012-01-10 Impact factor: 15.419

4. Pardon the Interruption: A Modification of Fischer's Venerable Reaction for the Synthesis of Heterocycles and Natural Products.

Authors: Robert B Susick; Lucas A Morrill; Elias Picazo; Neil K Garg
Journal: Synlett Date: 2017 Impact factor: 2.454

5. Recent developments in the catalytic, asymmetric construction of pyrroloindolines bearing all-carbon quaternary stereocenters.

Authors: Lindsay M Repka; Sarah E Reisman
Journal: J Org Chem Date: 2013-12-02 Impact factor: 4.354

Review 10. Advances in the Asymmetric Total Synthesis of Natural Products Using Chiral Secondary Amine Catalyzed Reactions of α,β-Unsaturated Aldehydes.

Authors: Zhonglei Wang
Journal: Molecules Date: 2019-09-19 Impact factor: 4.411