Literature DB >> 11681967

Catalytic, asymmetric synthesis of siphonarienal.

M A Calter1, W Liao, J A Struss.   

Abstract

This paper describes the synthesis of the marine natural product, siphonarienal. The key step of this synthesis is an aldol reaction that constructs most of the skeleton and sets all three stereocenters of the target in one step from commercially available starting materials. Deoxygenation and chain homologation steps complete the synthesis.

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Year:  2001        PMID： 11681967     DOI： 10.1021/jo0160367

Source DB:  PubMed          Journal:  J Org Chem        ISSN： 0022-3263            Impact factor:   4.354


  6 in total

1.  Catalytic, asymmetric reactions of ketenes and ketene enolates.

Authors:  Daniel H Paull; Anthony Weatherwax; Thomas Lectka
Journal:  Tetrahedron       Date:  2009-08-22       Impact factor: 2.457

2.  Catalytic Asymmetric Synthesis of Ketene Heterodimer β-Lactones: Scope and Limitations.

Authors:  Shi Chen; Ahmad A Ibrahim; Nicholas J Peraino; Divya Nalla; Mukulesh Mondal; Maxwell Van Raaphorst; Nessan J Kerrigan
Journal:  J Org Chem       Date:  2016-08-12       Impact factor: 4.354

3.  Asymmetric Synthesis of Deoxypropionate Derivatives via Catalytic Hydrogenolysis of Enantioenriched Z-Ketene Heterodimers.

Authors:  Shi Chen; Ahmad A Ibrahim; Mukulesh Mondal; Anthony J Magee; Adam J Cruz; Kraig A Wheeler; Nessan J Kerrigan
Journal:  Org Lett       Date:  2015-06-23       Impact factor: 6.005

4.  An efficient and general route to reduced polypropionates via Zr-catalyzed asymmetric CC bond formation.

Authors:  Ei-Ichi Negishi; Ze Tan; Bo Liang; Tibor Novak
Journal:  Proc Natl Acad Sci U S A       Date:  2004-04-08       Impact factor: 11.205

5.  Asymmetric synthesis, structure, and reactivity of unexpectedly stable spiroepoxy-beta-lactones including facile conversion to tetronic acids: application to (+)-maculalactone A.

Authors:  Richard J Duffy; Kay A Morris; Ravikrishna Vallakati; Wei Zhang; Daniel Romo
Journal:  J Org Chem       Date:  2009-07-03       Impact factor: 4.354

6.  Asymmetric Synthesis of Dipropionate Derivatives through Catalytic Hydrogenation of Enantioenriched E-Ketene Heterodimers.

Authors:  Shi Chen; Mukulesh Mondal; Ahmad A Ibrahim; Kraig A Wheeler; Nessan J Kerrigan
Journal:  Synthesis (Stuttg)       Date:  2016-04-12       Impact factor: 3.157
  6 in total

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