Total synthesis and biological evaluation of atrop-O-benzyl-desmethylabyssomicin CElectronic supplementary information (ESI) available: Experimental procedures, spectral data and copies of NMR spectra for all compounds, computational details. CCDC 992966. For ESI and crystallographic data in CIF or other electronic format see DOI: 10.1039/c4ob01436g

The total synthesis of desmethylabyssomicin C analogue 1 was accomplished using diastereotopos-selective ring closing metathesis and Nozaki-Hiyama-Kishi cyclization as the key steps. The synthetic analogue retained its antibacterial activity against methicillin-resistant S. aureus strains, whereas its cytotoxicity decreased for three orders of magnitude, as compared to atrop-abyssomicin C. The desmethyl analogue of abyssomicin C was synthesized. The synthetic analogue retained its antibacterial activity, whereas its cytotoxicity decreased for three orders of magnitude, as compared to the natural product.