Literature DB >> 18593171

Efficient and selective syntheses of (all-E)- and (6E,10Z)-2'-O-methylmyxalamides D via Pd-catalyzed alkenylation--carbonyl olefination synergy.

Guangwei Wang1, Zhihong Huang, Ei-Ichi Negishi.   

Abstract

Highly efficient and selective syntheses of both (all- E) and (6 E,10 Z)-isomers of 2'- O-methylmyxalamide D ( 2 and 3), in which the crucial conjugated pentaene moieties were assembled in > or =98% stereoselectivity through the use of two Pd-catalyzed alkenylation reactions, the Horner-Wadsworth-Emmons (HWE) olefination, and either the Corey-Schlessinger-Mills modified (CSM-modified) Peterson olefination for 2 or the Still-Gennari olefination for 3, are reported. Either 2 or 3 was prepared in 16% yield in seven steps from propargyl alcohol.

Entities:  

Mesh：

Substances：

Year:  2008        PMID： 18593171      PMCID： PMC2593746          DOI： 10.1021/ol801115s

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


  17 in total

1.  Synthesis (and alternative proof of configuration) of the scyphostatin C(1')-C(20') trienoyl fragment.

Authors:  T R Hoye; M A Tennakoon
Journal:  Org Lett       Date:  2000-05-18       Impact factor: 6.005

2.  Efficient and selective synthesis of 6,7-Dehydrostipiamide via Zr-catalyzed asymmetric carboalumination and Pd-catalyzed cross-coupling of organozincs.

Authors:  Xingzhong Zeng; Fanxing Zeng; Ei-ichi Negishi
Journal:  Org Lett       Date:  2004-09-16       Impact factor: 6.005

3.  Total synthesis of (-)-archazolid B.

Authors:  Paul A Roethle; Ingrid T Chen; Dirk Trauner
Journal:  J Am Chem Soc       Date:  2007-06-27       Impact factor: 15.419

Review 4.  Palladium complexes of N-heterocyclic carbenes as catalysts for cross-coupling reactions--a synthetic chemist's perspective.

Authors:  Eric Assen B Kantchev; Christopher J O'Brien; Michael G Organ
Journal:  Angew Chem Int Ed Engl       Date:  2007       Impact factor: 15.336

5.  Widely applicable Pd-catalyzed trans-selective monoalkylation of unactivated 1,1-dichloro-1-alkenes and Pd-catalyzed second substitution for the selective synthesis of E or Z trisubstituted alkenes.

Authors:  Ze Tan; Ei-Ichi Negishi
Journal:  Angew Chem Int Ed Engl       Date:  2006-01-23       Impact factor: 15.336

6.  Catalytic, efficient, and syn-selective construction of deoxypolypropionates and other chiral compounds via Zr-catalyzed asymmetric carboalumination of allyl alcohol.

Authors:  Bo Liang; Tibor Novak; Ze Tan; Ei-ichi Negishi
Journal:  J Am Chem Soc       Date:  2006-03-08       Impact factor: 15.419

7.  Total synthesis of 2'-O-methylmyxalamide D and (6E)-2'-O-methylmyxalamide D.

Authors:  Robert S Coleman; Xiaoling Lu; Isabelle Modolo
Journal:  J Am Chem Soc       Date:  2007-03-15       Impact factor: 15.419

8.  Highly stereo- and regioselective synthesis of (Z)-trisubstituted alkenes via 1-bromo-1-alkyne hydroboration-migratory insertion-Zn-promoted iodinolysis and Pd-catalyzed organozinc cross-coupling.

Authors:  Zhihong Huang; Ei-ichi Negishi
Journal:  J Am Chem Soc       Date:  2007-11-07       Impact factor: 15.419

9.  Recent advances in efficient and selective synthesis of di-, tri-, and tetrasubstituted alkenes via Pd-catalyzed alkenylation-carbonyl olefination synergy.

Authors:  Ei-ichi Negishi; Zhihong Huang; Guangwei Wang; Swathi Mohan; Chao Wang; Hatsuhiko Hattori
Journal:  Acc Chem Res       Date:  2008-11-18       Impact factor: 22.384

10.  1,4-Pentenyne as a five-carbon synthon for efficient and selective syntheses of natural products containing 2,4-dimethyl-1-penten-1,5-ylidene and related moieties by means of Zr-catalyzed carboalumination of alkynes and alkenes.

Authors:  Gangguo Zhu; Ei-ichi Negishi
Journal:  Chemistry       Date:  2008       Impact factor: 5.236
View more
  5 in total

1.  Arylethyne Bromoboration-Negishi Coupling Route to E- or Z-Aryl-Substituted Trisubstituted Alkenes of ≥98% IsomericPurity. New Horizon in the Highly Selective Synthesis of Trisubstituted Alkenes.

Authors:  Chao Wang; Zhaoqing Xu; Tomas Tobrman; Ei-Ichi Negishi
Journal:  Adv Synth Catal       Date:  2010-03-08       Impact factor: 5.837

2.  Highly selective synthesis of conjugated dienoic and trienoic esters via alkyne elementometalation-Pd-catalyzed cross-coupling.

Authors:  Guangwei Wang; Swathi Mohan; Ei-ichi Negishi
Journal:  Proc Natl Acad Sci U S A       Date:  2011-06-27       Impact factor: 11.205

3.  A strategy for the late-stage divergent syntheses of scyphostatin analogues.

Authors:  Jacob Y Cha; G Leslie Burnett; Yaodong Huang; Jarrod B Davidson; Thomas R R Pettus
Journal:  J Org Chem       Date:  2011-01-21       Impact factor: 4.354

4.  Alkyne elementometalation-Pd-catalyzed cross-coupling. Toward synthesis of all conceivable types of acyclic alkenes in high yields, efficiently, selectively, economically, and safely: "green" way.

Authors:  Ei-Ichi Negishi; Guangwei Wang; Honghua Rao; Zhaoqing Xu
Journal:  J Org Chem       Date:  2010-05-21       Impact factor: 4.354

5.  Synthesis of most polyene natural product motifs using just 12 building blocks and one coupling reaction.

Authors:  Eric M Woerly; Jahnabi Roy; Martin D Burke
Journal:  Nat Chem       Date:  2014-06       Impact factor: 24.427
  5 in total

北京卡尤迪生物科技股份有限公司 © 2022-2023.