Literature DB >> 21834570

Formal synthesis of (+)-sorangicin A.

Michael T Crimmins1, Matthew W Haley, Elizabeth A O'Bryan.   

Abstract

The formal synthesis of (+)-sorangicin A was completed by two independent routes. Both approaches feature a cross metathesis reaction to form the C29-C30 bond to arrive at the bicyclic ether/tetrahydropyran fragment. Formation of the C15-C16 olefin to unite the dihydropyran fragment with the rest of the molecule was achieved by either a cross metathesis reaction or a Julia-Kocienski olefination.

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Year:  2011        PMID: 21834570      PMCID: PMC3163046          DOI: 10.1021/ol201920j

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


  13 in total

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Authors:  V S Enev; H Kaehlig; J Mulzer
Journal:  J Am Chem Soc       Date:  2001-10-31       Impact factor: 15.419

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Authors:  Anjum Ahmed; E Kate Hoegenauer; Valentin S Enev; Martin Hanbauer; Hanspeter Kaehlig; Elisabeth Ohler; Johann Mulzer
Journal:  J Org Chem       Date:  2003-04-18       Impact factor: 4.354

3.  Total synthesis of (+)-sorangicin A.

Authors:  Amos B Smith; Shuzhi Dong; Jehrod B Brenneman; Richard J Fox
Journal:  J Am Chem Soc       Date:  2009-09-02       Impact factor: 15.419

4.  Asymmetric total synthesis of spongistatins 1 and 2.

Authors:  Michael T Crimmins; Jason D Katz; David G Washburn; Shawn P Allwein; Laura F McAtee
Journal:  J Am Chem Soc       Date:  2002-05-22       Impact factor: 15.419

5.  (+)-Sorangicin A synthetic studies. Construction of the C(1-15) and C(16-29) subtargets.

Authors:  Amos B Smith; Richard J Fox; John A Vanecko
Journal:  Org Lett       Date:  2005-07-07       Impact factor: 6.005

6.  Reactions of alkenylchromium reagents prepared from alkenyl trifluoromethanesulfonates (triflates) with chromium(II) chloride under nickel catalysis.

Authors:  K Takai; M Tagashira; T Kuroda; K Oshima; K Utimoto; H Nozaki
Journal:  J Am Chem Soc       Date:  1986-09-01       Impact factor: 15.419

7.  An efficient, second-generation synthesis of the signature dioxabicyclo[3.2.1]octane core of (+)-sorangicin A and elaboration of the (Z,Z,E)-triene acid system.

Authors:  Amos B Smith; Shuzhi Dong
Journal:  Org Lett       Date:  2009-03-05       Impact factor: 6.005

8.  Construction of a C(30-38) dioxabicyclo[3.2.1]octane subtarget for (+)-sorangicin A, exploiting a regio- and stereocontrolled acid-catalyzed epoxide ring opening.

Authors:  Amos B Smith; Richard J Fox
Journal:  Org Lett       Date:  2004-04-29       Impact factor: 6.005

9.  Iodine-catalyzed highly diastereoselective synthesis of trans-2,6-disubstituted-3,4-dihydropyrans: application to concise construction of C28-C37 bicyclic core of (+)-sorangicin A.

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10.  Continuum of mechanisms for nucleophilic substitutions of cyclic acetals.

Authors:  Jennifer R Krumper; Walter A Salamant; K A Woerpel
Journal:  Org Lett       Date:  2008-10-10       Impact factor: 6.005

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  3 in total

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Authors:  Ming Chen; William R Roush
Journal:  Org Lett       Date:  2012-02-28       Impact factor: 6.005

2.  (+)-Sorangicin A: evolution of a viable synthetic strategy.

Authors:  Amos B Smith; Shuzhi Dong; Richard J Fox; Jehrod B Brenneman; John A Vanecko; Tomohiro Maegawa
Journal:  Tetrahedron       Date:  2011-12-23       Impact factor: 2.457

3.  Total Synthesis of Cytospolide Q.

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Journal:  ACS Omega       Date:  2018-07-05
  3 in total

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