Literature DB >> 16522072

Enantioselective synthesis of pentacycloanammoxic acid.

Vincent Mascitti1, E J Corey.   

Abstract

A highly effective enantioselective synthesis of pentacycloanammoxic acid (1), an unusual naturally occurring fatty acid from Candidatus Brocadia anammoxidans, has been accomplished. The C20-structure of 1 was assembled with stereocontrol from four building blocks, cyclobutene, 2-cyclopentenone, the chiral silylcyclopentenone 6, and 7-bromoheptanoic acid. Both 1 and its enantiomer are now available in quantities that should facilitate future studies on the mode of biosynthesis which appears to be unprecedented.

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Year:  2006        PMID： 16522072     DOI： 10.1021/ja058370g

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


  14 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

2.  Optical signatures of molecular dissymmetry: combining theory with experiments to address stereochemical puzzles.

Authors:  Parag Mukhopadhyay; Peter Wipf; David N Beratan
Journal:  Acc Chem Res       Date:  2009-06-16       Impact factor: 22.384

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

Authors:  Saner Poplata; Andreas Tröster; You-Quan Zou; Thorsten Bach
Journal:  Chem Rev       Date:  2016-03-28       Impact factor: 60.622

4.  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

5.  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

6.  Stereodivergent synthesis of enantioenriched 4-hydroxy-2-cyclopentenones.

Authors:  Gurpreet Singh; Angelica Meyer; Jeffrey Aubé
Journal:  J Org Chem       Date:  2013-12-20       Impact factor: 4.354

7.  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

8.  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

9.  Lessons in Strain and Stability: Enantioselective Synthesis of (+)-[5]-Ladderanoic Acid.

Authors:  Erin N Hancock; Erin L Kuker; Dean J Tantillo; M Kevin Brown
Journal:  Angew Chem Int Ed Engl       Date:  2019-11-18       Impact factor: 15.336

Review 10.  Ladderane Natural Products: From the Ground Up.

Authors:  Erin N Hancock; M Kevin Brown
Journal:  Chemistry       Date:  2020-10-14       Impact factor: 5.020
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