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Literature DB >> 11463314

N-methoxy-N-acylnitrenium ions: application to the formal synthesis of (+/-)-desmethylamino FR901483.

Abstract

[reaction: see text] The formal synthesis of (+/-)-desmethylamino FR901483 (2) is described. Construction of the unique azatricyclic skeleton of 2 was accomplished by a sequence which involved (i) preparation of dienone 7 by an N-methoxy-N-acylnitrenium ion-induced spirocyclization, (ii) formation of 2-azabicyclo[3.3.1]nonane 5 by the 6-(pi-exo)-exo-trig radical cyclization of 1,7-enyne 6, and (iii) installation of the C-5 p-methoxybenzyl side chain by Lewis acid-mediated alkylation of silyl enol ether 18.

Entities: Chemical

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Year: 2001 PMID： 11463314 DOI： 10.1021/ol0161514

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

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Cited

11 in total

1. A Synthesis of the Tricyclic Core Structure of FR901483 Featuring an Ugi Four-Component Coupling and a Remarkably Selective Elimination Reaction.

Authors: Hirofumi Seike; Erik J Sorensen
Journal: Synlett Date: 2008-03-18 Impact factor: 2.454

2. Nitrenium ion azaspirocyclization-spirodienone cleavage: a new synthetic strategy for the stereocontrolled preparation of highly substituted lactams and N-hydroxy lactams.

Authors: Duncan J Wardrop; Matthew S Burge
Journal: J Org Chem Date: 2005-12-09 Impact factor: 4.354

Review 3. Chemistry of polyvalent iodine.

Authors: Viktor V Zhdankin; Peter J Stang
Journal: Chem Rev Date: 2008-12 Impact factor: 60.622

N-methoxy-N-acylnitrenium ions: application to the formal synthesis of (+/-)-desmethylamino FR901483.

1. A Synthesis of the Tricyclic Core Structure of FR901483 Featuring an Ugi Four-Component Coupling and a Remarkably Selective Elimination Reaction.

2. Nitrenium ion azaspirocyclization-spirodienone cleavage: a new synthetic strategy for the stereocontrolled preparation of highly substituted lactams and N-hydroxy lactams.

Review 3. Chemistry of polyvalent iodine.

4. Nitrenium ion-mediated alkene bis-cyclofunctionalization: total synthesis of (-)-swainsonine.

5. Synthetic studies toward (-)-FR901483 using a conjugate allylation to install the C-1 quaternary carbon.

6. Enantioselective Synthesis of the Tricyclic Core of FR901483 Featuring a Rh-Catalyzed [2+2+2] Cycloaddition.

7. Intramolecular oxamidation of unsaturated O-alkyl hydroxamates: a remarkably versatile entry to hydroxy lactams.

8. Studies on a total synthesis of the microbial immunosuppresive agent FR901483.

9. Toward the total synthesis of FR901483: concise synthesis of the azatricyclic skeleton.

10. Synthesis of Benzannulated Medium-ring Lactams via a Tandem Oxidative Dearomatization-Ring Expansion Reaction.