Literature DB >> 19123794

Organometallic enantiomeric scaffolding. Sequential semipinacol/1,5-"Michael-like" reactions as a strategic approach to bridgehead-quaternary center aza[3.3.1]bicyclics: application to the total synthesis of (-)-adaline.

Thomas C Coombs1, Yongqiang Zhang, Ethel C Garnier-Amblard, Lanny S Liebeskind.   

Abstract

A nontraditional approach to the enantiocontrolled construction of quaternary center-bearing heteroatom-bridged bicyclo[3.3.1]nonanes (homotropanes) is reported that is based on organometallic enantiomeric scaffolding. This strategy takes advantage of the unique reactivity profiles of TpMo(CO)(2)(5-oxo-eta(3)-pyranyl) and TpMo(CO)(2)(5-oxo-eta(3)-pyridinyl) scaffolds, and features a molybdenum-mediated semipinacol/1,5-"Michael-like" reaction sequence to establish the quaternary center and synthesize the bridged bicyclic structure. An asymmetric total synthesis of (-)-adaline highlights this methodology.

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Year:  2009        PMID： 19123794      PMCID： PMC2654255          DOI： 10.1021/ja808533z

Source DB:  PubMed          Journal:  J Am Chem Soc        ISSN： 0002-7863            Impact factor:   15.419


  16 in total

1.  Chiral scaffolds for enantiocontrolled synthesis: enantio- and regiocontrolled [4+2] cycloaddition to 3-alkenyl-n(3)-pyranylmolybdenum complexes.

Authors:  R G Arrayás; L S Liebeskind
Journal:  J Am Chem Soc       Date:  2001-06-27       Impact factor: 15.419

2.  Enantiocontrolled synthesis of highly functionalized tropanes via [5 + 2] cycloaddition to eta(3)-pyridinylmolybdenum pi-complexes.

Authors:  H C Malinakova; L S Liebeskind
Journal:  Org Lett       Date:  2000-11-30       Impact factor: 6.005

3.  Synthesis of substituted oxa- and aza[3.2.1] and [4.3.1]bicyclics via an unprecedented molybdenum-mediated 1,5-"Michael-type" reaction.

Authors:  Yongqiang Zhang; Lanny S Liebeskind
Journal:  J Am Chem Soc       Date:  2005-08-17       Impact factor: 15.419

4.  Stereo- and regiocontrolled construction of trisubstituted piperidines using a TpMo(CO)(2)(dihydropyridine) scaffold (Tp = hydridotrispyrazolylborate).

Authors:  A F Moretto; L S Liebeskind
Journal:  J Org Chem       Date:  2000-11-03       Impact factor: 4.354

5.  Organometallic enantiomeric scaffolding: organometallic chirons. Total synthesis of (-)-Bao Gong Teng A by a molybdenum-mediated [5 + 2] cycloaddition.

Authors:  Yongqiang Zhang; Lanny S Liebeskind
Journal:  J Am Chem Soc       Date:  2006-01-18       Impact factor: 15.419

6.  Asymmetric synthesis of (-)-adaline.

Authors:  Toshimasa Itoh; Naoki Yamazaki; Chihiro Kibayashi
Journal:  Org Lett       Date:  2002-07-25       Impact factor: 6.005

7.  The enantiomeric scaffold approach to highly functionalized 1-oxadecalines: enantio- and regiocontrolled [4 + 2] cycloadditions of 5-alkenyl-eta3-pyranylmolybdenum complexes.

Authors:  Ramón Gómez Arrayás; Jingjun Yin; Lanny S Liebeskind
Journal:  J Am Chem Soc       Date:  2007-02-14       Impact factor: 15.419

8.  Catalytic asymmetric synthesis of all-carbon quaternary stereocenters.

Authors:  Christopher J Douglas; Larry E Overman
Journal:  Proc Natl Acad Sci U S A       Date:  2004-01-14       Impact factor: 11.205

Review 9.  Contiguous stereogenic quaternary carbons: a daunting challenge in natural products synthesis.

Authors:  Emily A Peterson; Larry E Overman
Journal:  Proc Natl Acad Sci U S A       Date:  2004-07-01       Impact factor: 11.205

10.  Eta3-pyranyl and eta3-pyridinyl molybdenum pi-complexes as chiral scaffolds for the enantioselective construction of substituted oxa- and aza[3.3.1]bicyclics: first enantio- and regiocontrolled [5+3] cycloaddition reactions.

Authors:  Ramón Gómez Arrayás; Lanny S Liebeskind
Journal:  J Am Chem Soc       Date:  2003-07-30       Impact factor: 15.419
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  5 in total

1.  Organometallic enantiomeric scaffolding: a strategy for the enantiocontrolled construction of regio- and stereodivergent trisubstituted piperidines from a common precursor.

Authors:  Heilam Wong; Ethel C Garnier-Amblard; Lanny S Liebeskind
Journal:  J Am Chem Soc       Date:  2011-04-22       Impact factor: 15.419

2.  Novel Substitutions of 1-Alkoxy- and 1-Arylsulfonyloxy-η-Allylmolybdenum Complexes. A Case for η-Alkenyl Carbene Complexes as Intermediates.

Authors:  Thomas C Coombs; Wenwei Huang; Ethel C Garnier-Amblard; Lanny S Liebeskind
Journal:  Organometallics       Date:  2010-11-08       Impact factor: 3.876

3.  Organometallic enantiomeric scaffolding. A molybdenum-mediated intramolecular nucleophilic ketalization-demetalation cascade. Total synthesis of (+)-(1R,2S,5S,7R)-2-hydroxy-exo-brevicomin.

Authors:  Bo Cheng; Lanny S Liebeskind
Journal:  Org Lett       Date:  2009-08-20       Impact factor: 6.005

4.  A new reaction motif: "homo-S(N)2'-like" direct nucleophilic addition to neutral eta(3)-allylmolybdenum complexes. total synthesis of the antimalarial (+)-isofebrifugine.

Authors:  Wenyong Chen; Lanny S Liebeskind
Journal:  J Am Chem Soc       Date:  2009-09-09       Impact factor: 15.419

Review 5.  Recent progress in the synthesis of homotropane alkaloids adaline, euphococcinine and N-methyleuphococcinine.

Authors:  Dimas J P Lima; Antonio E G Santana; Michael A Birkett; Ricardo S Porto
Journal:  Beilstein J Org Chem       Date:  2021-01-05       Impact factor: 2.883
  5 in total

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