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Literature DB >> 22309201

Synthetic studies directed toward dideoxy lomaiviticinone lead to unexpected 1,2-oxazepine and isoxazole formation.

Aleksandra Baranczak¹, Gary A Sulikowski.

Abstract

In the course of studies directed toward the synthesis of dideoxy lomaiviticinone, 3-(nitromethyl)cyclohexenones 2a (X = H) and 2b (X = I) were prepared. The corresponding enolates were reacted with naphthazarin (1) and unexpectedly afforded 1,2-oxazepine 3 and isoxazole 4, respectively. Rationale for their formation is proposed.

Entities: Chemical Disease Gene

Mesh：

Substances：

Year: 2012 PMID： 22309201 PMCID： PMC3292050 DOI： 10.1021/ol203390w

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

12 in total

Review 1. Conjugate additions of nitroalkanes to electron-poor alkenes: recent results.

Authors: Roberto Ballini; Giovanna Bosica; Dennis Fiorini; Alessandro Palmieri; Marino Petrini
Journal: Chem Rev Date: 2005-03 Impact factor: 60.622

2. 11-Step enantioselective synthesis of (-)-lomaiviticin aglycon.

Authors: Seth B Herzon; Liang Lu; Christina M Woo; Shivajirao L Gholap
Journal: J Am Chem Soc Date: 2011-01-31 Impact factor: 15.419

3. Enantioselective synthesis of the lomaiviticin aglycon full carbon skeleton reveals remarkable remote substituent effects during the dimerization event.

Authors: Hong Geun Lee; Jae Young Ahn; Amy S Lee; Matthew D Shair
Journal: Chemistry Date: 2010-11-22 Impact factor: 5.236

4. Stereocontrolled synthesis of model core systems of lomaiviticins A and B.

Authors: K C Nicolaou; Ross M Denton; Achim Lenzen; David J Edmonds; Ang Li; Robert R Milburn; Scott T Harrison
Journal: Angew Chem Int Ed Engl Date: 2006-03-20 Impact factor: 15.336

5. Synthesis of the fully glycosylated cyclohexenone core of lomaiviticin A.

Authors: Shivajirao L Gholap; Christina M Woo; P C Ravikumar; Seth B Herzon
Journal: Org Lett Date: 2009-10-01 Impact factor: 6.005

Review 6. The diazofluorene antitumor antibiotics: structural elucidation, biosynthetic, synthetic, and chemical biological studies.

Authors: Seth B Herzon; Christina M Woo
Journal: Nat Prod Rep Date: 2011-10-28 Impact factor: 13.423

7. Synthesis of the N-(tert-butyloxycarbonyl)-O-triisopropylsilyl-D-pyrrolosamine Glycal of Lomaiviticin A & B via Epimerization of L-Threonine.

Authors: William J Morris; Matthew D Shair
Journal: Tetrahedron Lett Date: 2010-08-18 Impact factor: 2.415

Synthetic studies directed toward dideoxy lomaiviticinone lead to unexpected 1,2-oxazepine and isoxazole formation.

Review 1. Conjugate additions of nitroalkanes to electron-poor alkenes: recent results.

2. 11-Step enantioselective synthesis of (-)-lomaiviticin aglycon.

3. Enantioselective synthesis of the lomaiviticin aglycon full carbon skeleton reveals remarkable remote substituent effects during the dimerization event.

4. Stereocontrolled synthesis of model core systems of lomaiviticins A and B.

5. Synthesis of the fully glycosylated cyclohexenone core of lomaiviticin A.

Review 6. The diazofluorene antitumor antibiotics: structural elucidation, biosynthetic, synthetic, and chemical biological studies.

7. Synthesis of the N-(tert-butyloxycarbonyl)-O-triisopropylsilyl-D-pyrrolosamine Glycal of Lomaiviticin A & B via Epimerization of L-Threonine.

8. Synthesis of the monomeric unit of the lomaiviticin aglycon.

9. Stereocontrolled assembly of the C3/C3' dideoxy core of lomaiviticin A/B and congeners.

10. Stereoselective synthesis of 2-deoxy-beta-glycosides using anomeric O-alkylation/arylation.

1. Multigram Synthesis of 1-O-Acetyl-3-O-(4-methoxybenzyl)-4-N-(9-fluorenylmethoxycarbonyl)-4-N-methyl-L-pyrrolosamine.

2. Stereocontrolled Synthesis of the Fully Glycosylated Monomeric Unit of Lomaiviticin A.

3. Development of enantioselective synthetic routes to (-)-kinamycin F and (-)-lomaiviticin aglycon.

4. Studies toward the synthesis of the epoxykinamycin FL-120B': discovery of a decarbonylative photocyclization.

5. Structure Revision of the Lomaiviticins.

6. Synthesis of the bis(cyclohexenone) core of (-)-lomaiviticin A.