2. Academic Validation
  3. Total synthesis of phoslactomycin A

Total synthesis of phoslactomycin A

  • Org Lett. 2009 Jul 2;11(13):2728-31. doi: 10.1021/ol900757k.
Christian M König 1,  Björn Gebhardt,  Cornelia Schleth,  Mario Dauber,  Ulrich Koert
Affiliations

Affiliation

  • 1 Fachbereich Chemie, Philipps-University Marburg, Hans-Meerwein-Strasse, D-35032 Marburg, Germany.
PMID: 19485355 DOI: 10.1021/ol900757k
Abstract

A convergent total synthesis of the PP2A-inhibitor phoslactomycin A was achieved using a CuTC-mediated coupling of an alkenyl iodide C1-C13 fragment with an C14-C21 alkenyl stannane in the presence of a protected phosphate. Key features for the assembly of the C1-C13 fragment were an asymmetric dihydroxylation, an Evans-Aldol reaction, and a well-balanced protective group strategy. An asymmetric 1,4-addition to cyclohexenone was the key step in the preparation of the C14-C21 fragment.

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