Total synthesis of (−)-nakadomarin AElectronic supplementary information (ESI) available: Experimental procedures, ‘matched’ and ‘mismatched’ substrate and catalyst control studies and spectral data for all new compounds. CCDC reference numbers 805604, 805605. For ESI and crystallographic data in CIF or other electronic format see DOI: 10.1039/c1cc13665h

A highly diastereoselective bifunctional organocatalyst controlled Michael addition, a nitro-Mannich/lactamization cascade, a furan N-acyliminium cyclisation, a sequential alkyne RCM/syn-reduction and an alkene RCM has allowed a 19 step, highly stereoselective synthesis of (−)-nakadomarin A. [ABSTRACT FROM AUTHOR]