Literature DB >> 16468765

A concise total synthesis of (-)-cylindricine C through a stereoselective intramolecular aza-[3 + 3] annulation strategy.

Jacob J Swidorski1, Jiashi Wang, Richard P Hsung.   

Abstract

[reaction: see text] An enantioselective total synthesis of (-)-cylindricine C is described, featuring a diastereoselective intramolecular aza-[3 + 3] annulation strategy and an interesting halohydrin formation of the C4-5 olefin for construction of C4-ketone. This work provides a unique approach to this family of natural products.

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Year:  2006        PMID： 16468765     DOI： 10.1021/ol053059p

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


  11 in total

Review 1.  Studies on total synthesis of the cylindricine/fasicularin/lepadiformine family of tricyclic marine alkaloids.

Authors:  Steven M Weinreb
Journal:  Chem Rev       Date:  2006-06       Impact factor: 60.622

2.  Total synthesis of lepadiformine alkaloids using N-Boc α-amino nitriles as trianion synthons.

Authors:  Matthew A Perry; Matthew D Morin; Brian W Slafer; Scott D Rychnovsky
Journal:  J Org Chem       Date:  2012-03-13       Impact factor: 4.354

3.  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

4.  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

5.  Asymmetric aza-[3+3] annulation in the synthesis of indolizidines: an unexpected reversal of regiochemistry.

Authors:  Grant S Buchanan; Huifang Dai; Richard P Hsung; Aleksey I Gerasyuto; Casi M Scheinebeck
Journal:  Org Lett       Date:  2011-07-25       Impact factor: 6.005

6.  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

7.  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

8.  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

9.  Catalytic, asymmetric indolizidinone aza-quaternary stereocenter synthesis: expedient synthesis of the cylindricine alkaloid core.

Authors:  Derek M Dalton; Tomislav Rovis
Journal:  Org Lett       Date:  2013-04-30       Impact factor: 6.005

10.  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
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