Literature DB >> 18630880

Concise total synthesis of (+)-crocacin C.

Gopal Sirasani1, Tapas Paul, Rodrigo B Andrade.   

Abstract

The cytotoxic natural product (+)-crocacin C ( 1) has been synthesized in 10 linear steps from commercially available Evans' chiral propionimide in 5% overall yield (8 steps from Evans' chiral dipropionate synthon). No protecting groups were utilized.

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Year:  2008        PMID: 18630880     DOI: 10.1021/jo800906p

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


  4 in total

1.  Enantioselective synthesis of (+)-crocacin C. An example of a highly challenging mismatched double asymmetric δ-stannylcrotylboration reaction.

Authors:  Ming Chen; William R Roush
Journal:  Org Lett       Date:  2012-03-12       Impact factor: 6.005

Review 2.  Protecting-group-free synthesis as an opportunity for invention.

Authors:  Ian S Young; Phil S Baran
Journal:  Nat Chem       Date:  2009-06       Impact factor: 24.427

3.  Iterative Cross-Couplng with MIDA Boronates: Towards a General Platform for Small Molecule Synthesis.

Authors:  Eric P Gillis; Martin D Burke
Journal:  Aldrichimica Acta       Date:  2009       Impact factor: 3.667

4.  Multistep synthesis of complex boronic acids from simple MIDA boronates.

Authors:  Eric P Gillis; Martin D Burke
Journal:  J Am Chem Soc       Date:  2008-10-07       Impact factor: 15.419

  4 in total

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