Literature DB >> 16320991

Sequential cycloaddition approach to the tricyclic core of vibsanin E. Total synthesis of (+/-)-5-epi-10-epi-vibsanin E.

Huw M L Davies1, Øystein Loe, Douglas G Stafford.   

Abstract

[chemical reaction: see text]. A direct access to (+/-)-5-epi-10-epi-vibsanin E is described, based on three key cycloaddition steps, a rhodium-catalyzed [4 + 3] cycloaddition, a heteronuclear [4 + 2] cycloaddition, and a photochemically induced [4 + 2] cycloaddition.

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Year:  2005        PMID： 16320991     DOI： 10.1021/ol052005c

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


  7 in total

1.  Towards the Total Synthesis of 3-Hydroxyvibsanin E.

Authors:  Brett D Schwartz; Justin R Denton; Paul V Bernhardt; Huw M L Davies; Craig M Williams
Journal:  Synthesis (Stuttg)       Date:  2009-09-01       Impact factor: 3.157

2.  Total Synthesis of (±)-Vibsanin E.

Authors:  Brett D Schwartz; Justin R Denton; Huw M L Davies; Craig M Williams
Journal:  Aust J Chem       Date:  2009       Impact factor: 1.321

3.  Asymmetric [4 + 3] cycloadditions between vinylcarbenoids and dienes: application to the total synthesis of the natural product (-)-5-epi-vibsanin E.

Authors:  Brett D Schwartz; Justin R Denton; Yajing Lian; Huw M L Davies; Craig M Williams
Journal:  J Am Chem Soc       Date:  2009-06-17       Impact factor: 15.419

Review 4.  Recent applications of the divinylcyclopropane-cycloheptadiene rearrangement in organic synthesis.

Authors:  Sebastian Krüger; Tanja Gaich
Journal:  Beilstein J Org Chem       Date:  2014-01-16       Impact factor: 2.883

Review 5.  Photochemical Approaches to Complex Chemotypes: Applications in Natural Product Synthesis.

Authors:  Markus D Kärkäs; John A Porco; Corey R J Stephenson
Journal:  Chem Rev       Date:  2016-04-27       Impact factor: 60.622

6.  Photochemical syntheses, transformations, and bioorthogonal chemistry of trans-cycloheptene and sila trans-cycloheptene Ag(i) complexes.

Authors:  Yinzhi Fang; Han Zhang; Zhen Huang; Samuel L Scinto; Jeffrey C Yang; Christopher W Am Ende; Olga Dmitrenko; Douglas S Johnson; Joseph M Fox
Journal:  Chem Sci       Date:  2018-01-08       Impact factor: 9.825

7.  End game strategies towards the total synthesis of vibsanin E, 3-hydroxyvibsanin E, furanovibsanin A, and 3-O-methylfuranovibsanin A.

Authors:  Brett D Schwartz; Craig M Williams; Paul V Bernhardt
Journal:  Beilstein J Org Chem       Date:  2008-10-08       Impact factor: 2.883
  7 in total

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