Literature DB >> 10814270

Enantioselective syntheses of 2-alkyl- and 2,6-dialkylpiperidine alkaloids: preparations of the hydrochlorides of (-)-coniine, (-)-solenopsin A, and (-)-dihydropinidine.

T J Wilkinson1, N W Stehle, P Beak.   

Abstract

[reaction: see text] Sequences of lithiation-substitution, enantioselective hydrogenation, and diastereoselective lithiation-substitution provide efficient highly enantioselective syntheses of 2-substituted and cis and trans 2,6-disubstituted piperidines. The methodology is demonstrated by syntheses of (-)-coniine, (-)-solenopsin A, and (-)-dihydropinidine as their hydrochlorides.

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Year:  2000        PMID： 10814270     DOI： 10.1021/ol9912534

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


  9 in total

1.  CATALYTIC DYNAMIC RESOLUTION APPLIED TO THE SYNTHESIS OF 2,6-DISUBSTITUTED PIPERIDINES: PREPARATION OF (+)-LUPETIDINE AND (-)-EPIDIHYDROPINIDINE.

Authors:  Timothy K Beng; Robert E Gawley
Journal:  Heterocycles       Date:  2012-01-01       Impact factor: 0.831

2.  Stereocontrolled synthesis of vicinally functionalized piperidines by nucleophilic β-addition of alkyllithiums to α-aryl substituted piperidine enecarbamates.

Authors:  Timothy K Beng; Hironori Takeuchi; Manuel Weber; Richmond Sarpong
Journal:  Chem Commun (Camb)       Date:  2015-05-04       Impact factor: 6.222

3.  The Pauson-Khand Reaction as a New Entry to the Synthesis of Bridged Bicyclic Heterocycles: Application to the Enantioselective Total Synthesis of (-)-Alstonerine.

Authors:  Kenneth A Miller; Charles S Shanahan; Stephen F Martin
Journal:  Tetrahedron       Date:  2008       Impact factor: 2.457

Review 4.  Control of asymmetry in the radical addition approach to chiral amine synthesis.

Authors:  Gregory K Friestad
Journal:  Top Curr Chem       Date:  2014

5.  Solenopsin A and analogs exhibit ceramide-like biological activity.

Authors:  Isabella Karlsson; Xin Zhou; Raquela Thomas; Allorie T Smith; Michael Y Bonner; Pooja Bakshi; Ajay K Banga; J Phillip Bowen; Ghassan Qabaja; Shavon L Ford; Matthew D Ballard; Kimberly S Petersen; Xuechen Li; Guangping Chen; Besim Ogretmen; Jin Zhang; E Blake Watkins; Rebecca S Arnold; Jack L Arbiser
Journal:  Vasc Cell       Date:  2015-05-08

6.  Generation and electrophile trapping of N-Boc-2-lithio-2-azetine: synthesis of 2-substituted 2-azetines.

Authors:  David M Hodgson; Christopher I Pearson; Madiha Kazmi
Journal:  Org Lett       Date:  2014-01-10       Impact factor: 6.005

7.  Expanding metabolic pathway for de novo biosynthesis of the chiral pharmaceutical intermediate L-pipecolic acid in Escherichia coli.

Authors:  Hanxiao Ying; Sha Tao; Jing Wang; Weichao Ma; Kequan Chen; Xin Wang; Pingkai Ouyang
Journal:  Microb Cell Fact       Date:  2017-03-27       Impact factor: 5.328

8.  Structural Basis for Recognition of L-lysine, L-ornithine, and L-2,4-diamino Butyric Acid by Lysine Cyclodeaminase.

Authors:  Kyungjin Min; Hye-Jin Yoon; Atsushi Matsuura; Yong Hwan Kim; Hyung Ho Lee
Journal:  Mol Cells       Date:  2018-04-05       Impact factor: 5.034

9.  Solenopsin, the alkaloidal component of the fire ant (Solenopsis invicta), is a naturally occurring inhibitor of phosphatidylinositol-3-kinase signaling and angiogenesis.

Authors:  Jack L Arbiser; Tweeny Kau; Martha Konar; Krishna Narra; Ramani Ramchandran; Scott A Summers; Chris J Vlahos; Keqiang Ye; Betsy N Perry; William Matter; Anthony Fischl; James Cook; Pamela A Silver; Jenny Bain; Philip Cohen; David Whitmire; Scott Furness; Baskaran Govindarajan; J Phillip Bowen
Journal:  Blood       Date:  2006-09-21       Impact factor: 22.113
  9 in total

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