Literature DB >> 23101616

Enantioselective synthesis of a hydroxymethyl-cis-1,3-cyclopentenediol building block.

Robert A Craig1, Jennifer L Roizen, Russell C Smith, Amanda C Jones, Brian M Stoltz.   

Abstract

A brief, enantioselective synthesis of a hydroxymethyl-cis-1,3-cyclopentenediol building block is presented. This scaffold allows access to the cis-1,3-cyclopentanediol fragments found in a variety of biologically active natural and non-natural products. This rapid and efficient synthesis is highlighted by the utilization of the palladium-catalyzed enantioselective allylic alkylation of dioxanone substrates to prepare tertiary alcohols.

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Year:  2012        PMID： 23101616      PMCID： PMC3506031          DOI： 10.1021/ol3027297

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


  14 in total

Review 1.  Perspectives on the structural and biosynthetic interrelationships between oxygenated furanocembranoids and their polycyclic congeners found in corals.

Authors:  Yi Li; Gerald Pattenden
Journal:  Nat Prod Rep       Date:  2011-06-03       Impact factor: 13.423

2.  The enantioselective Tsuji allylation.

Authors:  Douglas C Behenna; Brian M Stoltz
Journal:  J Am Chem Soc       Date:  2004-11-24       Impact factor: 15.419

Review 3.  Enantioselective Tsuji allylations.

Authors:  Justin T Mohr; Brian M Stoltz
Journal:  Chem Asian J       Date:  2007-12-03

Review 4.  The chemistry of marine furanocembranoids, pseudopteranes, gersolanes, and related natural products.

Authors:  Paul A Roethle; Dirk Trauner
Journal:  Nat Prod Rep       Date:  2008-02-25       Impact factor: 13.423

5.  Convergent total synthesis of (+)-ophiobolin A.

Authors:  Kazuhiro Tsuna; Naoyoshi Noguchi; Masahisa Nakada
Journal:  Angew Chem Int Ed Engl       Date:  2011-09-13       Impact factor: 15.336

6.  The catalytic enantioselective total synthesis of (+)-liphagal.

Authors:  Joshua J Day; Ryan M McFadden; Scott C Virgil; Helene Kolding; Jennifer L Alleva; Brian M Stoltz
Journal:  Angew Chem Int Ed Engl       Date:  2011-06-10       Impact factor: 15.336

7.  A mild, convenient, and inexpensive procedure for conversion of vinyl halides to alpha-haloketones.

Authors:  Michael P VanBrunt; Reuben O Ambenge; Steven M Weinreb
Journal:  J Org Chem       Date:  2003-04-18       Impact factor: 4.354

8.  Total synthesis of prostaglandins F2-alpha and E2 as the naturally occurring forms.

Authors:  E J Corey; T K Schaaf; W Huber; U Koelliker; N M Weinshenker
Journal:  J Am Chem Soc       Date:  1970-01-28       Impact factor: 15.419

9.  Total synthesis of (-)-neplanocin a by using lithium thiolate-initiated Michael-aldol tandem cyclization reaction.

Authors:  M Ono; K Nishimura; H Tsubouchi; Y Nagaoka; K Tomioka
Journal:  J Org Chem       Date:  2001-11-30       Impact factor: 4.354

10.  Catalytic enantioselective alkylation of substituted dioxanone enol ethers: ready access to Calpha-tetrasubstituted hydroxyketones, acids, and esters.

Authors:  Masaki Seto; Jennifer L Roizen; Brian M Stoltz
Journal:  Angew Chem Int Ed Engl       Date:  2008       Impact factor: 15.336
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  8 in total

1.  Development of a Unified Enantioselective, Convergent Synthetic Approach Toward the Furanobutenolide-Derived Polycyclic Norcembranoid Diterpenes: Asymmetric Formation of the Polycyclic Norditerpenoid Carbocyclic Core by Tandem Annulation Cascade.

Authors:  Robert A Craig; Russell C Smith; Jennifer L Roizen; Amanda C Jones; Scott C Virgil; Brian M Stoltz
Journal:  J Org Chem       Date:  2018-03-19       Impact factor: 4.354

Review 2.  Polycyclic Furanobutenolide-Derived Cembranoid and Norcembranoid Natural Products: Biosynthetic Connections and Synthetic Efforts.

Authors:  Robert A Craig; Brian M Stoltz
Journal:  Chem Rev       Date:  2017-05-18       Impact factor: 60.622

3.  Preparation of 1,5-Dioxaspiro[5.5]undecan-3-one.

Authors:  Robert A Craig; Russell C Smith; Beau P Pritchett; Benzi I Estipona; Brian M Stoltz
Journal:  Organic Synth       Date:  2016

4.  Model Studies To Access the [6,7,5,5]-Core of Ineleganolide Using Tandem Translactonization-Cope or Cyclopropanation-Cope Rearrangements as Key Steps.

Authors:  Jennifer L Roizen; Amanda C Jones; Russell C Smith; Scott C Virgil; Brian M Stoltz
Journal:  J Org Chem       Date:  2017-11-21       Impact factor: 4.354

5.  Synthesis and Exploration of Electronically Modified (R)-5,5-Dimethyl-(p-CF3)3-i-PrPHOX in Palladium-Catalyzed Enantio- and Diastereoselective Allylic Alkylation: A Practical Alternative to (R)-(p-CF3)3-t-BuPHOX.

Authors:  Robert A Craig; Brian M Stoltz
Journal:  Tetrahedron Lett       Date:  2015-08-05       Impact factor: 2.415

6.  Catalytic enantioselective total synthesis of (+)-eucomic acid.

Authors:  Benzi I Estipona; Beau P Pritchett; Robert A Craig; Brian M Stoltz
Journal:  Tetrahedron       Date:  2016-03-02       Impact factor: 2.457

7.  Enantioselective, Convergent Synthesis of the Ineleganolide Core by a Tandem Annulation Cascade.

Authors:  Robert A Craig; Jennifer L Roizen; Russell C Smith; Amanda C Jones; Scott C Virgil; Brian M Stoltz
Journal:  Chem Sci       Date:  2016-08-17       Impact factor: 9.825

Review 8.  The Allylic Alkylation of Ketone Enolates.

Authors:  Lukas Junk; Uli Kazmaier
Journal:  ChemistryOpen       Date:  2020-09-10       Impact factor: 2.630
  8 in total

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