Literature DB >> 12049506

A novel and highly stereoselective approach to aza-spirocycles. A short total synthesis of 2-epi-(+/-)-perhydrohistrionicotoxin and an unprecedented decarboxylation of 2-pyrones.

Michael J McLaughlin1, Richard P Hsung, Kevin P Cole, Juliet M Hahn, Jiashi Wang.   

Abstract

[reaction: see text] A novel and highly stereoselective synthesis of aza-spirocycles is described. An application of this methodology is illustrated as a short and concise total synthesis of 2-epi-(+/-)-perhydrohistrionicotoxin with high diastereomeric control at the aza-spirocenter. An unprecedented decarboxylation of the 2-pyrone ring is observed in this total synthesis effort.

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Year:  2002        PMID： 12049506     DOI： 10.1021/ol020052o

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


  7 in total

1.  Highly torquoselective electrocyclizations and competing 1,7-hydrogen shifts of 1-azatrienes with silyl substitution at the allylic carbon.

Authors:  Zhi-Xiong Ma; Ashay Patel; K N Houk; Richard P Hsung
Journal:  Org Lett       Date:  2015-04-10       Impact factor: 6.005

2.  Aza-[3 + 3] Annulations: A New Unified Strategy in Alkaloid Synthesis.

Authors:  Grant S Buchanan; John B Feltenberger; Richard P Hsung
Journal:  Curr Org Synth       Date:  2010-08-01       Impact factor: 1.975

3.  A Stereodivergent Approach for Accessing Both C2,8a-Syn and C2,8a-Anti Relative Stereochemical Manifolds in the Lepadin Family via a TiCL(4)-Promoted Aza-[3 + 3] Annulation.

Authors:  Gang Li; Lauren J Carlson; Irina K Sagamanova; Brian W Slafer; Richard P Hsung; Claudio Gilardi; Heather M Sklenicka; Nadiya Sydroenko
Journal:  Synthesis (Stuttg)       Date:  2009-09-01       Impact factor: 3.157

4.  Aza- and Carbo-[3 + 3] Annulations of Exo-Cyclic Vinylogous Amides and Urethanes. Synthesis of Tetrahydroindolizidines and An Unexpected Formation of Hexahydroquinolines.

Authors:  Sunil K Ghosh; Grant S Buchanan; Quincy A Long; Yonggang Wei; Ziyad F Al-Rashid; Heather M Sklenicka; Richard P Hsung
Journal:  Tetrahedron       Date:  2008-01-28       Impact factor: 2.457

5.  Total synthesis of (+)-lepadin F.

Authors:  Gang Li; Richard P Hsung; Brian W Slafer; Irina K Sagamanova
Journal:  Org Lett       Date:  2008-09-27       Impact factor: 6.005

6.  A General Approach to the Quinolizidine Alkaloids via an Intramolecular Aza-[3 + 3] Annulation. Synthesis of (±)-2-Deoxy-Lasubine II.

Authors:  Yu Zhang; Aleksey I Gerasyuto; Quincy A Long; Richard P Hsung
Journal:  Synlett       Date:  2008-01-01       Impact factor: 2.454

7.  Establishing the concept of aza-[3 + 3] annulations using enones as a key expansion of this unified strategy in alkaloid synthesis.

Authors:  Aleksey I Gerasyuto; Zhi-Xiong Ma; Grant S Buchanan; Richard P Hsung
Journal:  Beilstein J Org Chem       Date:  2013-06-18       Impact factor: 2.883
  7 in total

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