Literature DB >> 18215048

Asymmetric [4+3] cycloadditions between benzofuranyldiazoacetates and dienes: formal synthesis of (+)-frondosin B.

Jeremy P Olson1, Huw M L Davies.   

Abstract

The reaction of benzofuranyldiazoacetates with 1,3-dienes catalyzed by the dirhodium tetracarboxylate Rh2(R-DOSP)4, generates formal [4+3] cycloadducts with >94% de and 91-98% ee. The reaction proceeds by a tandem cyclopropanation/Cope rearrangement followed by a stereoselective tautomerization. This methodology was extended to a formal synthesis of (+)-frondosin B.

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Year:  2008        PMID： 18215048     DOI： 10.1021/ol702844g

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


  15 in total

1.  Reversal of the regiochemistry in the rhodium-catalyzed [4+3] cycloaddition between vinyldiazoacetates and dienes.

Authors:  Pablo E Guzmán; Yajing Lian; Huw M L Davies
Journal:  Angew Chem Int Ed Engl       Date:  2014-09-29       Impact factor: 15.336

2.  Gold-catalyzed Intermolecular [4C + 3C] Cycloaddition Reactions.

Authors:  Benjamin W Gung; Lauren N Bailey; Josh Wonser
Journal:  Tetrahedron Lett       Date:  2010-04-28       Impact factor: 2.415

3.  The organocatalytic three-step total synthesis of (+)-frondosin B.

Authors:  Maud Reiter; Staffan Torssell; Sandra Lee; David W C Macmillan
Journal:  Chem Sci       Date:  2010-07       Impact factor: 9.825

4.  Catalyst-controlled formal [4 + 3] cycloaddition applied to the total synthesis of (+)-barekoxide and (-)-barekol.

Authors:  Yajing Lian; Laura C Miller; Stephen Born; Richmond Sarpong; Huw M L Davies
Journal:  J Am Chem Soc       Date:  2010-09-08       Impact factor: 15.419

5.  Enantioselective synthesis of 2,2,5-tri- and 2,2,5,5-tetrasubstituted tetrahydrofurans via [4 + 2] cycloaddition and ring-opening cross-metathesis.

Authors:  Noah M Benjamin; Stephen F Martin
Journal:  Org Lett       Date:  2011-01-06       Impact factor: 6.005

6.  Platinum-Catalyzed α,β-Unsaturated Carbene Formation in the Formal Syntheses of Frondosin B and Liphagal.

Authors:  Khoi Q Huynh; Curtis A Seizert; Tarik J Ozumerzifon; Paul A Allegretti; Eric M Ferreira
Journal:  Org Lett       Date:  2016-12-20       Impact factor: 6.005

7.  Asymmetric synthesis of seven-membered carbocyclic rings via a sequential oxyanionic 5-exo-dig cyclization/claisen rearrangement process. Total synthesis of (-)-frondosin B.

Authors:  Timo V Ovaska; Jonathan A Sullivan; Sami I Ovaska; Jacob B Winegrad; Justin D Fair
Journal:  Org Lett       Date:  2009-06-18       Impact factor: 6.005

8.  Divergent outcomes of carbene transfer reactions from dirhodium- and copper-based catalysts separately or in combination.

Authors:  Xinfang Xu; Wen-Hao Hu; Peter Y Zavalij; Michael P Doyle
Journal:  Angew Chem Int Ed Engl       Date:  2011-10-06       Impact factor: 15.336

Review 9.  Application of donor/acceptor-carbenoids to the synthesis of natural products.

Authors:  Huw M L Davies; Justin R Denton
Journal:  Chem Soc Rev       Date:  2009-09-30       Impact factor: 54.564

10.  Rhodium- and platinum-catalyzed [4+3] cycloaddition with concomitant indole annulation: synthesis of cyclohepta[b]indoles.

Authors:  Dongxu Shu; Wangze Song; Xiaoxun Li; Weiping Tang
Journal:  Angew Chem Int Ed Engl       Date:  2013-02-10       Impact factor: 15.336
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