Literature DB >> 19093836

Enantioselective total synthesis of (+)-cassiol.

Krastina V Petrova1, Justin T Mohr, Brian M Stoltz.   

Abstract

An enantioselective total synthesis of (+)-cassiol is reported. The complex derived from Pd(2)(pmdba)(3) and enantiopure t-BuPHOX ligand catalyzes enantioconvergent decarboxylative alkylation to generate the quaternary carbon stereocenter at an early stage. The overall synthetic strategy involves a convergent late-stage coupling of two fragments. The synthesis features a longest linear sequence of eight steps.

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Year:  2009        PMID： 19093836      PMCID： PMC2707596          DOI： 10.1021/ol802410t

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


  17 in total

1.  The enantioselective Tsuji allylation.

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

2.  Toward the Development of a General Chiral Auxiliary. 5. High Diastereofacial Selectivity in Cycloadditions with Trienol Silyl Ethers: An Application to an Enantioselective Synthesis of (-)-Cassioside.

Authors:  Robert K Boeckman; Yugang Liu
Journal:  J Org Chem       Date:  1996-11-15       Impact factor: 4.354

3.  Synthesis of the carbocyclic core of zoanthenol: implementation of an unusual acid-catalyzed cyclization.

Authors:  Douglas C Behenna; Jennifer L Stockdill; Brian M Stoltz
Journal:  Angew Chem Int Ed Engl       Date:  2007       Impact factor: 15.336

Review 4.  Enantioselective Tsuji allylations.

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

5.  The catalytic asymmetric total synthesis of elatol.

Authors:  David E White; Ian C Stewart; Robert H Grubbs; Brian M Stoltz
Journal:  J Am Chem Soc       Date:  2007-12-29       Impact factor: 15.419

Review 6.  Natural products as inspiration for the development of asymmetric catalysis.

Authors:  Justin T Mohr; Michael R Krout; Brian M Stoltz
Journal:  Nature       Date:  2008-09-18       Impact factor: 49.962

7.  The total synthesis of (-)-cyanthiwigin F by means of double catalytic enantioselective alkylation.

Authors:  John A Enquist; Brian M Stoltz
Journal:  Nature       Date:  2008-06-26       Impact factor: 49.962

8.  Improved procedure for the oxidative cleavage of olefins by OsO4-NaIO4.

Authors:  Wensheng Yu; Yan Mei; Ying Kang; Zhengmao Hua; Zhendong Jin
Journal:  Org Lett       Date:  2004-09-16       Impact factor: 6.005

9.  Catalytic asymmetric synthesis of all-carbon quaternary stereocenters.

Authors:  Christopher J Douglas; Larry E Overman
Journal:  Proc Natl Acad Sci U S A       Date:  2004-01-14       Impact factor: 11.205

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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  18 in total

1.  Synthesis of enantioenriched γ-quaternary cycloheptenones using a combined allylic alkylation/Stork-Danheiser approach: preparation of mono-, bi-, and tricyclic systems.

Authors:  Nathan B Bennett; Allen Y Hong; Andrew M Harned; Brian M Stoltz
Journal:  Org Biomol Chem       Date:  2011-10-19       Impact factor: 3.876

2.  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

3.  Assembly of the Limonoid Architecture by a Divergent Approach: Total Synthesis of (±)-Andirolide N via (±)-8α-Hydroxycarapin.

Authors:  Alexander W Schuppe; Timothy R Newhouse
Journal:  J Am Chem Soc       Date:  2017-01-05       Impact factor: 15.419

4.  Palladium-Catalyzed Asymmetric Alkylation in the Synthesis of Cyclopentanoid and Cycloheptanoid Core Structures Bearing All-Carbon Quaternary Stereocenters.

Authors:  Allen Y Hong; Nathan B Bennett; Michael R Krout; Thomas Jensen; Andrew M Harned; Brian M Stoltz
Journal:  Tetrahedron       Date:  2011-12-30       Impact factor: 2.457

5.  Enantioselective decarboxylative alkylation reactions: catalyst development, substrate scope, and mechanistic studies.

Authors:  Douglas C Behenna; Justin T Mohr; Nathaniel H Sherden; Smaranda C Marinescu; Andrew M Harned; Kousuke Tani; Masaki Seto; Sandy Ma; Zoltán Novák; Michael R Krout; Ryan M McFadden; Jennifer L Roizen; John A Enquist; David E White; Samantha R Levine; Krastina V Petrova; Akihiko Iwashita; Scott C Virgil; Brian M Stoltz
Journal:  Chemistry       Date:  2011-11-14       Impact factor: 5.236

6.  Enantioconvergent synthesis of (+)-aphanorphine via asymmetric Pd-catalyzed alkene carboamination.

Authors:  Duy N Mai; Brandon R Rosen; John P Wolfe
Journal:  Org Lett       Date:  2011-05-10       Impact factor: 6.005

7.  Expanding insight into asymmetric palladium-catalyzed allylic alkylation of N-heterocyclic molecules and cyclic ketones.

Authors:  Nathan B Bennett; Douglas C Duquette; Jimin Kim; Wen-Bo Liu; Alexander N Marziale; Douglas C Behenna; Scott C Virgil; Brian M Stoltz
Journal:  Chemistry       Date:  2013-02-27       Impact factor: 5.236

8.  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

9.  Catalytic enantioselective approach to the eudesmane sesquiterpenoids: total synthesis of (+)-carissone.

Authors:  Samantha R Levine; Michael R Krout; Brian M Stoltz
Journal:  Org Lett       Date:  2009-01-15       Impact factor: 6.005

10.  Enantioselective total synthesis of the reported structures of (-)-9-epi-presilphiperfolan-1-ol and (-)-presilphiperfolan-1-ol: structural confirmation and reassignment and biosynthetic insights.

Authors:  Allen Y Hong; Brian M Stoltz
Journal:  Angew Chem Int Ed Engl       Date:  2012-08-22       Impact factor: 15.336
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