Literature DB >> 17319675

A formal synthesis of psymberin.

Ning Shangguan1, Sezgin Kiren, Lawrence J Williams.   

Abstract

A formal synthesis of psymberin (irciniastatin A) is presented. Notable features of the synthesis include the chemo-, regio-, and stereoselective oxidation of a 1,3-disubstituted allene, a configuration-dependent spirodiepoxide opening, the efficient syntheses of functionalized trans-2,6-disubstituted pyrans, and the union of a highly functionalized aldehyde with a pentasubstituted aryl homoenolate to give a dihydroisocumarin. [structure: see text]

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Year:  2007        PMID: 17319675     DOI: 10.1021/ol063143k

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


  19 in total

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Authors:  Jared W Rigoli; Luke A Boralsky; John C Hershberger; Dagmara Marston; Alan R Meis; Ilia A Guzei; Jennifer M Schomaker
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Authors:  Tadeusz F Molinski; Brandon I Morinaka
Journal:  Tetrahedron       Date:  2012-11-18       Impact factor: 2.457

5.  Synthesis of 1,3-diaminated stereotriads via rearrangement of 1,4-diazaspiro[2.2]pentanes.

Authors:  Cale D Weatherly; Jared W Rigoli; Jennifer M Schomaker
Journal:  Org Lett       Date:  2012-03-20       Impact factor: 6.005

6.  Total synthesis of (+)-psymberin (irciniastatin A): catalytic reagent control as the strategic cornerstone.

Authors:  Amos B Smith; Jon A Jurica; Shawn P Walsh
Journal:  Org Lett       Date:  2008-12-18       Impact factor: 6.005

7.  A Convenient Reagent for Aldehyde to Alkyne Homologation.

Authors:  Douglass F Taber; Sha Bai; Peng-Fei Guo
Journal:  Tetrahedron Lett       Date:  2008-11-24       Impact factor: 2.415

8.  Spirodiepoxides: synthesis of epoxomicinoids.

Authors:  Yue Zhang; Joseph R Cusick; Partha Ghosh; Ning Shangguan; Sreenivas Katukojvala; Jennifer Inghrim; Thomas J Emge; Lawrence J Williams
Journal:  J Org Chem       Date:  2009-10-16       Impact factor: 4.354

9.  Progress toward the total synthesis of psymberin/irciniastatin A.

Authors:  Lauren E Brown; Yakira R Landaverry; James R Davies; Kristin A Milinkevich; Sandra Ast; Joseph S Carlson; Allen G Oliver; Joseph P Konopelski
Journal:  J Org Chem       Date:  2009-08-07       Impact factor: 4.354

10.  Studies toward the unique pederin family member psymberin: full structure elucidation, two alternative total syntheses, and analogs.

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Journal:  J Am Chem Soc       Date:  2012-10-04       Impact factor: 15.419

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