Literature DB >> 21667928

Asymmetric total syntheses of (-)-variabilin and (-)-glycinol.

Michael A Calter1, Na Li.   

Abstract

Total syntheses of (-)-variabilin and (-)-glycinol have been accomplished, using the catalytic, asymmetric "interrupted" Feist-Bénary reaction (IFB) as the key transformation to introduce both stereogenic centers. A monoquinidine pyrimidinyl ether catalyst affords the IFB products in over 90% ee in both cases. Other key steps include an intramolecular Buchwald-Hartwig coupling and a nickel-catalyzed aryl tosylate reduction.
© 2011 American Chemical Society

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Year:  2011        PMID： 21667928      PMCID： PMC3132817          DOI： 10.1021/ol201332u

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


  7 in total

1.  Heterogeneous catalysis with nickel-on-graphite (Ni/C(g)): reduction of aryl tosylates and mesylates.

Authors:  Bruce H Lipshutz; Bryan A Frieman; Tom Butler; Vladimir Kogan
Journal:  Angew Chem Int Ed Engl       Date:  2006-01-23       Impact factor: 15.336

2.  Induction of phytoalexin synthesis in soybean. Dimethylallylpyrophosphate:trihydroxypterocarpan dimethylallyl transferase from elicitor-induced cotyledons.

Authors:  U Zähringer; J Ebel; L J Mulheirn; R L Lyne; H Grisebach
Journal:  FEBS Lett       Date:  1979-05-01       Impact factor: 4.124

3.  Catalytic, asymmetric, "interrupted" Feist-Bénary reactions.

Authors:  Michael A Calter; Ryan M Phillips; Christine Flaschenriem
Journal:  J Am Chem Soc       Date:  2005-10-26       Impact factor: 15.419

4.  Flavonoids of Lonchocarpus montanus A.M.G. Azevedo and biological activity.

Authors:  Aderbal F Magalhães; Ana Maria G A Tozzi; Eva G Magalhães; Miriam Sannomiya; Maria del Pilar C Soriano; Mary A F Perez
Journal:  An Acad Bras Cienc       Date:  2007-09       Impact factor: 1.753

5.  Total syntheses of racemic and natural glycinol.

Authors:  Amarjit Luniwal; Rahul S Khupse; Michael Reese; Lei Fang; Paul W Erhardt
Journal:  J Nat Prod       Date:  2009-11       Impact factor: 4.050

6.  Induction of phytoalexin synthesis in soybean. Stereospecific 3,9-dihydroxypterocarpan 6a-hydroxylase from elicitor-induced soybean cell cultures.

Authors:  M L Hagmann; W Heller; H Grisebach
Journal:  Eur J Biochem       Date:  1984-07-02

7.  Identification of the potent phytoestrogen glycinol in elicited soybean (Glycine max).

Authors:  Stephen M Boué; Syreeta L Tilghman; Steven Elliott; M Carla Zimmerman; K Y Williams; Florastina Payton-Stewart; Allen P Miraflor; Melanie H Howell; Betty Y Shih; Carol H Carter-Wientjes; Chris Segar; Barbara S Beckman; Thomas E Wiese; Thomas E Cleveland; John A McLachlan; Matthew E Burow
Journal:  Endocrinology       Date:  2008-12-30       Impact factor: 4.736
  7 in total
  6 in total

1.  Direct Zinc(II)-Catalyzed Enantioconvergent Additions of Terminal Alkynes to α-Keto Esters.

Authors:  Blane P Zavesky; Jeffrey S Johnson
Journal:  Angew Chem Int Ed Engl       Date:  2017-06-20       Impact factor: 15.336

2.  Synthesis of Complex Tertiary Glycolates by Enantioconvergent Arylation of Stereochemically Labile α-Keto Esters.

Authors:  Samuel L Bartlett; Kimberly M Keiter; Jeffrey S Johnson
Journal:  J Am Chem Soc       Date:  2017-03-02       Impact factor: 15.419

3.  Dynamic kinetic asymmetric transformations of β-stereogenic α-ketoesters by direct aldolization.

Authors:  Michael T Corbett; Jeffrey S Johnson
Journal:  Angew Chem Int Ed Engl       Date:  2013-11-12       Impact factor: 15.336

4.  Stereodivergent organocatalytic intramolecular Michael addition/lactonization for the asymmetric synthesis of substituted dihydrobenzofurans and tetrahydrofurans.

Authors:  Dorine Belmessieri; Alix de la Houpliere; Ewen D D Calder; James E Taylor; Andrew D Smith
Journal:  Chemistry       Date:  2014-07-02       Impact factor: 5.236

5.  Asymmetric one-pot transformation of isoflavones to pterocarpans and its application in phytoalexin synthesis.

Authors:  Philipp Ciesielski; Peter Metz
Journal:  Nat Commun       Date:  2020-06-18       Impact factor: 14.919

6.  Flavonoids from the stems of Millettia pachyloba Drake mediate cytotoxic activity through apoptosis and autophagy in cancer cells.

Authors:  Wei Yan; Jianhong Yang; Huan Tang; Linlin Xue; Kai Chen; Lun Wang; Min Zhao; Minghai Tang; Aihua Peng; Chaofeng Long; Xiaoxin Chen; Haoyu Ye; Lijuan Chen
Journal:  J Adv Res       Date:  2019-06-21       Impact factor: 10.479
  6 in total

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