Literature DB >> 23594129

Trianion synthon approach to spirocyclic heterocycles.

Matthew A Perry1, Richard R Hill, Scott D Rychnovsky.   

Abstract

A variety of spirocyclic heterocycles have been constructed by a double-alkylation and reductive cyclization approach utilizing α-heteroatom nitriles as trianion synthons. The method provides access to heteroatom-substituted spirocycles in a variety of ring sizes that are found in natural products and are important in pharmaceutical lead development and optimization.

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Year:  2013        PMID： 23594129      PMCID： PMC3676279          DOI： 10.1021/ol400788q

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


  12 in total

1.  Stereoselectivity of intramolecular SN' cyclizations of alkyllithium reagents on methoxy alkenes.

Authors:  Thomas E La Cruz; Scott D Rychnovsky
Journal:  J Org Chem       Date:  2006-02-03       Impact factor: 4.354

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.  Tandem alkylation-Michael addition to vinylogous carbonates for the stereoselective construction of 2,3,3,6-tetrasubstituted tetrahydropyrans.

Authors:  Santosh J Gharpure; S Raja Bhushan Reddy
Journal:  Org Lett       Date:  2009-06-18       Impact factor: 6.005

4.  Nankakurine A, a novel C16N2-type alkaloid from Lycopodium hamiltonii.

Authors:  Yusuke Hirasawa; Hiroshi Morita; Jun'ichi Kobayashi
Journal:  Org Lett       Date:  2004-09-16       Impact factor: 6.005

5.  Cyclization via carbolithiation of alpha-amino alkyllithium reagents.

Authors:  Robert J Bahde; Scott D Rychnovsky
Journal:  Org Lett       Date:  2008-08-14       Impact factor: 6.005

6.  Structure based design: novel spirocyclic ethers as nonpeptidal P2-ligands for HIV protease inhibitors.

Authors:  A K Ghosh; K Krishnan; D E Walters; W Cho; H Cho; Y Koo; J Trevino; L Holland; J Buthod
Journal:  Bioorg Med Chem Lett       Date:  1998-04-21       Impact factor: 2.823

7.  Enantioselective synthesis of alpha-ionone derivatives using an anti S(N)2' substitution of functionalized zinc organometallics.

Authors:  Darunee Soorukram; Paul Knochel
Journal:  Org Lett       Date:  2004-07-08       Impact factor: 6.005

8.  Histrionicotoxins: roentgen-ray analysis of the novel allenic and acetylenie spiroalkaloids isolated from a Colombian frog, Dendrobates histrionicus.

Authors:  J W Daly; I Karle; C W Myers; T Tokuyama; J A Waters; B Witkop
Journal:  Proc Natl Acad Sci U S A       Date:  1971-08       Impact factor: 11.205

9.  FR901483, a novel immunosuppressant isolated from Cladobotryum sp. No. 11231. Taxonomy of the producing organism, fermentation, isolation, physico-chemical properties and biological activities.

Authors:  K Sakamoto; E Tsujii; F Abe; T Nakanishi; M Yamashita; N Shigematsu; S Izumi; M Okuhara
Journal:  J Antibiot (Tokyo)       Date:  1996-01       Impact factor: 2.649

10.  A reductive cyclization approach to attenol A.

Authors:  Thomas E La Cruz; Scott D Rychnovsky
Journal:  J Org Chem       Date:  2007-03-09       Impact factor: 4.354
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  2 in total

1.  Amino Azaxylylenes Photogenerated from o-Amido Imines: Photoassisted Access to Complex Spiro-Poly-Heterocycles.

Authors:  Olga A Mukhina; Dmitry M Kuznetsov; Teresa M Cowger; Andrei G Kutateladze
Journal:  Angew Chem Int Ed Engl       Date:  2015-06-30       Impact factor: 15.336

2.  Synthesis of 1-Azaspiro[4.4]nonane Derivatives Enabled by Domino Radical Bicyclization Involving Formation and Capture of Alkoxyaminyl Radicals.

Authors:  Alejandro Guerrero-Caicedo; Diana M Soto-Martínez; David A Osorio; Muskendol Novoa; Alix E Loaiza; Luz M Jaramillo-Gómez
Journal:  ACS Omega       Date:  2019-12-04
  2 in total

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