Literature DB >> 22432912

Enantioselective total synthesis of (+)-amabiline.

Timothy J Senter1, Olugbeminiyi O Fadeyi, Craig W Lindsley.   

Abstract

The first total synthesis of (+)-amabiline, an unsaturated pyrrolizidine alkaloid from Cynoglossum amabile, is reported. This convergent, enantioselective synthesis proceeds in 15 steps (10-step longest linear sequence) in 6.2% overall yield and features novel methodology to construct the unsaturated pyrrolizidine or (-)-supinidine core.

Entities:  

Mesh：

Substances：

Year:  2012        PMID： 22432912      PMCID： PMC3359844          DOI： 10.1021/ol300466a

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


  10 in total

1.  Highly diastereoselective and general synthesis of primary β-fluoroamines.

Authors:  Michael L Schulte; Craig W Lindsley
Journal:  Org Lett       Date:  2011-09-26       Impact factor: 6.005

Review 2.  Pyrrolizidine alkaloids.

Authors:  D J Robins
Journal:  Nat Prod Rep       Date:  1989-06       Impact factor: 13.423

3.  A chemoenzymatic total synthesis of (+)-amabiline.

Authors:  Alison D Findlay; Martin G Banwell
Journal:  Org Lett       Date:  2009-07-16       Impact factor: 6.005

4.  Low catalyst loadings in olefin metathesis: synthesis of nitrogen heterocycles by ring-closing metathesis.

Authors:  Kevin M Kuhn; Timothy M Champagne; Soon Hyeok Hong; Wen-Hao Wei; Andrew Nickel; Choon Woo Lee; Scott C Virgil; Robert H Grubbs; Richard L Pederson
Journal:  Org Lett       Date:  2010-03-05       Impact factor: 6.005

5.  Diastereoselective and enantioselective Rh(I)-catalyzed additions of arylboronic acids to N-tert-butanesulfinyl and N-diphenylphosphinoyl aldimines.

Authors:  Daniel J Weix; Yili Shi; Jonathan A Ellman
Journal:  J Am Chem Soc       Date:  2005-02-02       Impact factor: 15.419

6.  A rapid and general method for the asymmetric synthesis of 2-substituted pyrrolidines using tert-butanesulfinamide.

Authors:  Kristin M Brinner; Jonathan A Ellman
Journal:  Org Biomol Chem       Date:  2005-05-04       Impact factor: 3.876

7.  Cytotoxic and antimalarial alkaloids from the bulbs of Crinum amabile.

Authors:  K Likhitwitayawuid; C K Angerhofer; H Chai; J M Pezzuto; G A Cordell; N Ruangrungsi
Journal:  J Nat Prod       Date:  1993-08       Impact factor: 4.050

8.  Synthesis of pyrrolizidine alkaloids indicine, intermedine, lycopsamine, and analogues and their N-oxides. Potential antitumor agents.

Authors:  L H Zalkow; J A Glinski; L T Gelbaum; T J Fleischmann; L S McGowan; M M Gordon
Journal:  J Med Chem       Date:  1985-06       Impact factor: 7.446

9.  Asymmetric synthesis of beta-amino acid derivatives incorporating a broad range of substitution patterns by enolate additions to tert-butanesulfinyl imines.

Authors:  Tony P Tang; Jonathan A Ellman
Journal:  J Org Chem       Date:  2002-11-01       Impact factor: 4.354

10.  Asymmetric synthesis of alpha-branched allylic amines by the Rh(I)-catalyzed addition of alkenyltrifluoroborates to N-tert-butanesulfinyl aldimines.

Authors:  Katrien Brak; Jonathan A Ellman
Journal:  J Am Chem Soc       Date:  2009-03-25       Impact factor: 15.419
  10 in total
  5 in total

1.  Stereocontrolled Synthesis of a Potential Transition-State Inhibitor of the Salicylate Synthase MbtI from Mycobacterium tuberculosis.

Authors:  Zheng Liu; Feng Liu; Courtney C Aldrich
Journal:  J Org Chem       Date:  2015-06-16       Impact factor: 4.354

2.  Towards the Total Synthesis of Marineosin A: Construction of the Macrocyclic Pyrrole and an Advanced, Functionalized Spiroaminal Model.

Authors:  Leslie N Aldrich; Cynthia B Berry; Brittney S Bates; Leah C Konkol; Miranda So; Craig W Lindsley
Journal:  European J Org Chem       Date:  2013-07-01

3.  Total synthesis of stemaphylline N-oxide and related C9a-epimeric analogues.

Authors:  Michael L Schulte; Mark L Turlington; Sharangdhar S Phatak; Joel M Harp; Shaun R Stauffer; Craig W Lindsley
Journal:  Chemistry       Date:  2013-08-16       Impact factor: 5.236

4.  A General, Enantioselective Synthesis of 1-Azabicyclo[m.n.0]alkane Ring Systems.

Authors:  Timothy J Senter; Michael L Schulte; Leah C Konkol; Tyler E Wadzinski; Craig W Lindsley
Journal:  Tetrahedron Lett       Date:  2013-03-27       Impact factor: 2.415

Review 5.  N-tert-Butanesulfinyl imines in the asymmetric synthesis of nitrogen-containing heterocycles.

Authors:  Joseane A Mendes; Paulo R R Costa; Miguel Yus; Francisco Foubelo; Camilla D Buarque
Journal:  Beilstein J Org Chem       Date:  2021-05-12       Impact factor: 2.883
  5 in total

北京卡尤迪生物科技股份有限公司 © 2022-2023.