Literature DB >> 15571387

Total synthesis of (+/-)-pentacycloanammoxic acid.

Vincent Mascitti1, E J Corey.   

Abstract

The first total synthesis of (+/-)-pentacycloanammoxic acid/methyl ester (1), an unusual naturally occurring fatty acid from Candidatus Brocadia anammoxidans, has been accomplished by the sequence of reactions shown in Scheme 1. The C20-structure of 1 was assembled with stereocontrol from three building blocks: cyclooctatetraene, 2-cyclopentenone, and 7-bromoheptanoic acid. The synthesis of 1 confirms the proposed structure of 1. The mode of biosynthesis and absolute configuration have yet to be clarified.

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Year:  2004        PMID： 15571387     DOI： 10.1021/ja044089a

Source DB:  PubMed          Journal:  J Am Chem Soc        ISSN： 0002-7863            Impact factor:   15.419


  19 in total

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

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2.  Application of diazene-directed fragment assembly to the total synthesis and stereochemical assignment of (+)-desmethyl-meso-chimonanthine and related heterodimeric alkaloids.

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Review 3.  Radical-mediated dimerization and oxidation reactions for the synthesis of complex alkaloids.

Authors:  Stephen P Lathrop; Justin Kim; Mohammad Movassaghi
Journal:  Chimia (Aarau)       Date:  2012       Impact factor: 1.509

4.  Directed heterodimerization: stereocontrolled assembly via solvent-caged unsymmetrical diazene fragmentation.

Authors:  Mohammad Movassaghi; Omar K Ahmad; Stephen P Lathrop
Journal:  J Am Chem Soc       Date:  2011-08-01       Impact factor: 15.419

5.  Recent Advances in the Synthesis of Cyclobutanes by Olefin [2 + 2] Photocycloaddition Reactions.

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6.  Massive nitrogen loss from the Benguela upwelling system through anaerobic ammonium oxidation.

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Journal:  Proc Natl Acad Sci U S A       Date:  2005-04-20       Impact factor: 11.205

7.  Stereoselective preparation of cyclobutanes with four different substituents: total synthesis and structural revision of pipercyclobutanamide A and piperchabamide G.

Authors:  Renhe Liu; Min Zhang; Thomas P Wyche; Gabrielle N Winston-McPherson; Tim S Bugni; Weiping Tang
Journal:  Angew Chem Int Ed Engl       Date:  2012-06-19       Impact factor: 15.336

8.  Crystal engineering rescues a solution organic synthesis in a cocrystallization that confirms the configuration of a molecular ladder.

Authors:  Manza B J Atkinson; S V Santhana Mariappan; Dejan-Krešimir Bučar; Jonas Baltrusaitis; Tomislav Friščić; Naif G Sinada; Leonard R MacGillivray
Journal:  Proc Natl Acad Sci U S A       Date:  2011-06-20       Impact factor: 11.205

9.  Chemical Synthesis and Self-Assembly of a Ladderane Phospholipid.

Authors:  Jaron A M Mercer; Carolyn M Cohen; Steven R Shuken; Anna M Wagner; Myles W Smith; Frank R Moss; Matthew D Smith; Riku Vahala; Alejandro Gonzalez-Martinez; Steven G Boxer; Noah Z Burns
Journal:  J Am Chem Soc       Date:  2016-11-29       Impact factor: 15.419

10.  Synthesis of ent-[3]-Ladderanol: Development and Application of Intramolecular Chirality Transfer [2+2] Cycloadditions of Allenic Ketones and Alkenes.

Authors:  Nathan J Line; Brittany P Witherspoon; Erin N Hancock; M Kevin Brown
Journal:  J Am Chem Soc       Date:  2017-10-06       Impact factor: 15.419
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