Abstract
Total synthesis of (−)-enigmazole A, a marine macrolide natural product with cytotoxic activity, has been accomplished. The tetrahydropyran moiety was constructed by means of a domino olefin cross-metathesis/intramolecular oxa-Michael addition of a δ-hydroxy olefin. After coupling of advanced intermediates, the macrocycle was formed through gold-catalyzed rearrangement of a propargylic benzoate, followed by ring-closing metathesis of the resultant α,β-unsaturated ketone.
Original language | English |
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Pages (from-to) | 5143-5146 |
Number of pages | 4 |
Journal | Angewandte Chemie - International Edition |
Volume | 57 |
Issue number | 18 |
DOIs | |
Publication status | Published - 2018 Apr 23 |
Keywords
- macrocycles
- metathesis
- natural products
- rearrangement
- total synthesis
ASJC Scopus subject areas
- Catalysis
- Chemistry(all)