Literature DB >> 12123380

First asymmetric total synthesis of (+)-sparteine.

Brenton T Smith1, John A Wendt, Jeffrey Aubé.   

Abstract

[reaction: see text] The total synthesis of (+)-sparteine was accomplished from 2,5-norbornadione in 15 steps and 15.7% overall yield. The key steps were two ring-expansion reactions, one involving an intramolecular Schmidt reaction and one using a novel variant of the photo-Beckmann rearrangement.

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Year:  2002        PMID： 12123380     DOI： 10.1021/ol026230v

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


  8 in total

1.  Palladium-catalyzed enantioselective oxidation of chiral secondary alcohols: access to both enantiomeric series.

Authors:  David C Ebner; Raissa M Trend; Cédric Genet; Matthew J McGrath; Peter O'Brien; Brian M Stoltz
Journal:  Angew Chem Int Ed Engl       Date:  2008       Impact factor: 15.336

2.  Synthesis of the azaphilones (+)-sclerotiorin and (+)-8-O-methylsclerotiorinamine utilizing (+)-sparteine surrogates in copper-mediated oxidative dearomatization.

Authors:  Andrew R Germain; Daniel M Bruggemeyer; Jianglong Zhu; Cedric Genet; Peter O'Brien; John A Porco
Journal:  J Org Chem       Date:  2011-03-14       Impact factor: 4.354

Review 3.  Isolation and synthesis of cryptosanguinolentine (isocryptolepine), a naturally-occurring bioactive indoloquinoline alkaloid.

Authors:  Elida N Thobokholt; Enrique L Larghi; Andrea B J Bracca; Teodoro S Kaufman
Journal:  RSC Adv       Date:  2020-05-19       Impact factor: 4.036

4.  Synthesis of medium-bridged twisted lactams via cation-pi control of the regiochemistry of the intramolecular Schmidt reaction.

Authors:  Michal Szostak; Lei Yao; Jeffrey Aubé
Journal:  J Org Chem       Date:  2010-02-19       Impact factor: 4.354

5.  Lithium Amino Alkoxide-Evans Enolate Mixed Aggregates: Aldol Addition with Matched and Mismatched Stereocontrol.

Authors:  Janis Jermaks; Evan H Tallmadge; Ivan Keresztes; David B Collum
Journal:  J Am Chem Soc       Date:  2018-02-19       Impact factor: 15.419

6.  Asymmetric total synthesis of alkaloids 223A and 6-epi-223A.

Authors:  Partha Ghosh; Weston R Judd; Timothy Ribelin; Jeffrey Aubé
Journal:  Org Lett       Date:  2009-09-17       Impact factor: 6.005

7.  Probing chemical space with alkaloid-inspired libraries.

Authors:  Michael C McLeod; Gurpreet Singh; James N Plampin; Digamber Rane; Jenna L Wang; Victor W Day; Jeffrey Aubé
Journal:  Nat Chem       Date:  2014-01-19       Impact factor: 24.427

8.  Sustainable Asymmetric Organolithium Chemistry: Enantio- and Chemoselective Acylations through Recycling of Solvent, Sparteine, and Weinreb "Amine".

Authors:  Serena Monticelli; Wolfgang Holzer; Thierry Langer; Alexander Roller; Berit Olofsson; Vittorio Pace
Journal:  ChemSusChem       Date:  2019-02-13       Impact factor: 8.928
  8 in total

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