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Stereoselective Total Synthesis and Enantioselective Formal Synthesis of the Antineoplastic Sesquiterpene Quinone Metachromin A

Journal of the Brazilian Chemical Society, ISSN: 0103-5053, Vol: 10, Issue: 5, Page: 401-414
1999
  • 13
    Citations
  • 14,946
    Usage
  • 10
    Captures
  • 3
    Mentions
  • 0
    Social Media
Metric Options:   Counts1 Year3 Year

Metrics Details

  • Citations
    13
    • Citation Indexes
      13
  • Usage
    14,946
  • Captures
    10
  • Mentions
    3
    • References
      3
      • Wikipedia
        3

Article Description

The first total synthesis of the antineoplastic marine natural product metachromin-A (1) was accomplished through a convergent synthetic approach amenable to the preparation of analogues for biological studies. The synthesis involved twelve steps in its longest sequence and sixteen steps overall. The total synthesis of the racemic metachromin-A features: (1) an efficient synthesis of the quinone intermediate 11; (2) efficient protocols for the preparation of the key fragments 5 and 6; (3) a highly regioselective Thiele-Winter acetoxylation step; and (4) a stereoselective Horner-Wadsworth-Emmons coupling reaction employing fragment 6 as a non-stabilized phosphonate as an effective partner. The metachromin-A synthesis was made formally enantioselective by the asymmetric synthesis of fragment 5 employing the methodologies developed by Simpkins (asymmetric deprotonation with a chiral nitrogenated base) and d'Angelo (enantioselective deracemization). This latter protocol furnished fragment 5 with an enantiomeric excess of ∼85%, as determined by H-NMR spectroscopy.

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