Literature DB >> 12509882

Total synthesis of (-)-cassine.

Hidefumi Makabe1, Looi Kok Kong, Mitsuru Hirota.   

Abstract

The PdCl(2)-catalyzed cyclization of amino allylic alcohol 16 gave the cyclized product 17a with excellent diastereoselectivity. The versatility of compound 17a as the building block for synthesizing cis-2,6-disubstituted piperidine alkaloids has been demonstrated by a total synthesis of (-)-cassine (1). [reaction--see text]

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Year:  2003        PMID： 12509882     DOI： 10.1021/ol0201916

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


  9 in total

1.  Application of the aza-Achmatowicz oxidative rearrangement for the stereoselective synthesis of the Cassia and Prosopis alkaloid family.

Authors:  Carolyn A Leverett; Michael P Cassidy; Albert Padwa
Journal:  J Org Chem       Date:  2006-10-27       Impact factor: 4.354

2.  An alkyne hydrosilylation-oxidation strategy for the selective installation of oxygen functionality.

Authors:  Barry M Trost; Zachary T Ball; Kai M Laemmerhold
Journal:  J Am Chem Soc       Date:  2005-07-20       Impact factor: 15.419

3.  Gold(I)-catalyzed intramolecular amination of allylic alcohols with alkylamines.

Authors:  Paramita Mukherjee; Ross A Widenhoefer
Journal:  Org Lett       Date:  2011-02-11       Impact factor: 6.005

4.  Re2 O7 -Mediated Dehydrative Cyclization Reactions: Total Synthesis of Herboxidiene and Its 12-Desmethyl Analogue.

Authors:  Tyler M Rohrs; Qi Qin; Paul E Floreancig
Journal:  Angew Chem Int Ed Engl       Date:  2017-07-28       Impact factor: 15.336

5.  Asymmetric Synthesis of (+)-Iso-6-Cassine via Stereoselective Intramolecular Amidomercuration.

Authors:  Satwinder Singh; Om V Singh; Hyunsoo Han
Journal:  Tetrahedron Lett       Date:  2007-11-19       Impact factor: 2.415

6.  Evaluation of a non-prime site substituent and warheads combined with a decahydroisoquinolin scaffold as a SARS 3CL protease inhibitor.

Authors:  Kouji Ohnishi; Yasunao Hattori; Kazuya Kobayashi; Kenichi Akaji
Journal:  Bioorg Med Chem       Date:  2018-12-12       Impact factor: 3.641

7.  Fused-ring structure of decahydroisoquinolin as a novel scaffold for SARS 3CL protease inhibitors.

Authors:  Yasuhiro Shimamoto; Yasunao Hattori; Kazuya Kobayashi; Kenta Teruya; Akira Sanjoh; Atsushi Nakagawa; Eiki Yamashita; Kenichi Akaji
Journal:  Bioorg Med Chem       Date:  2014-12-20       Impact factor: 3.641

Review 8.  Biodiversity of sphingoid bases ("sphingosines") and related amino alcohols.

Authors:  Sarah T Pruett; Anatoliy Bushnev; Kerri Hagedorn; Madhura Adiga; Christopher A Haynes; M Cameron Sullards; Dennis C Liotta; Alfred H Merrill
Journal:  J Lipid Res       Date:  2008-05-21       Impact factor: 5.922

9.  Structural basis for the development of SARS 3CL protease inhibitors from a peptide mimic to an aza-decaline scaffold.

Authors:  Kenta Teruya; Yasunao Hattori; Yasuhiro Shimamoto; Kazuya Kobayashi; Akira Sanjoh; Atsushi Nakagawa; Eiki Yamashita; Kenichi Akaji
Journal:  Biopolymers       Date:  2016-11-04       Impact factor: 2.505
  9 in total

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