Literature DB >> 19093809

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

Samantha R Levine1, Michael R Krout, Brian M Stoltz.   

Abstract

A catalytic enantioselective approach to the eudesmane sesquiterpenoids is reported. The strategic use of a palladium-catalyzed enantioselective alkylation of vinylogous ester substrates forged the C(10) all-carbon quaternary center. This key transformation enabled a diastereoselective olefin hydrogenation to create the syn stereochemistry at C(7). The devised synthetic strategy allowed for the preparation of the antibacterial agent (+)-carissone and a formal synthesis of the P/Q-type calcium channel blocker (-)-alpha-eudesmol.

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Year:  2009        PMID： 19093809      PMCID： PMC2724392          DOI： 10.1021/ol802409h

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


  22 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.  Antibacterial activity of an eudesmane sesquiterpene isolated from common Varthemia, Varthemia iphionoides.

Authors:  Maher M Al-Dabbas; Fumio Hashinaga; Samir A M Abdelgaleil; Toshihiko Suganuma; Kohki Akiyama; Hideo Hayashi
Journal:  J Ethnopharmacol       Date:  2004-12-29       Impact factor: 4.360

Review 3.  Eudesmane sesquiterpenoids from the Asteraceae family.

Authors:  Quan-Xiang Wu; Yan-Ping Shi; Zhong-Jian Jia
Journal:  Nat Prod Rep       Date:  2006-08-07       Impact factor: 13.423

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.  Desymmetrizing hydroformylation with the aid of a planar chiral catalyst-directing group.

Authors:  Bernhard Breit; Daniel Breuninger
Journal:  J Am Chem Soc       Date:  2004-08-25       Impact factor: 15.419

8.  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

9.  Enantioselective total synthesis of (+)-cassiol.

Authors:  Krastina V Petrova; Justin T Mohr; Brian M Stoltz
Journal:  Org Lett       Date:  2009-01-15       Impact factor: 6.005

10.  Highly oxygenated guaianolides and eudesman-12-oic acids from Balsamorhiza sagittata and Balsamorhiza macrophylla.

Authors:  Abou El-Hamd H Mohamed; Ahmed A Ahmed; Eckhard Wollenweber; Bruce Bohm; Yoshinori Asakawa
Journal:  Chem Pharm Bull (Tokyo)       Date:  2006-02       Impact factor: 1.645
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  21 in total

1.  Deacylative allylation: allylic alkylation via retro-Claisen activation.

Authors:  Alexander J Grenning; Jon A Tunge
Journal:  J Am Chem Soc       Date:  2011-08-24       Impact factor: 15.419

2.  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

Review 3.  Transition metal-catalyzed decarboxylative allylation and benzylation reactions.

Authors:  Jimmie D Weaver; Antonio Recio; Alexander J Grenning; Jon A Tunge
Journal:  Chem Rev       Date:  2011-01-14       Impact factor: 60.622

4.  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

5.  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

6.  Total synthesis of eudesmane terpenes by site-selective C-H oxidations.

Authors:  Ke Chen; Phil S Baran
Journal:  Nature       Date:  2009-05-13       Impact factor: 49.962

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.  Enantioselective total synthesis of (+)-cassiol.

Authors:  Krastina V Petrova; Justin T Mohr; 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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