Self-Assembly of Disorazole C1 through a One-Pot Alkyne Metathesis Homodimerization Strategy.
Alkyne metathesis is increasingly explored as a reliable method to close macrocyclic rings, but there are no prior examples of an alkyne-metathesis-based homodimerization approach to natural products. In this approach to the cytotoxic C2-symmetric marine-derived bis(lactone) disorazole C1, a highly convergent, modular strategy is employed featuring cyclization through an ambitious one-pot alkyne cross-metathesis/ring-closing metathesis self-assembly process.
EaStCHEM School of Chemistry, University of Edinburgh, David Brewster Road, Edinburgh, EH9 3FJ (UK).
Kevin J
KJ
Ralston
EaStCHEM School of Chemistry, University of Edinburgh, David Brewster Road, Edinburgh, EH9 3FJ (UK).
H Clinton
HC
Ramstadius
EaStCHEM School of Chemistry, University of Edinburgh, David Brewster Road, Edinburgh, EH9 3FJ (UK).
Richard C
RC
Brewster
EaStCHEM School of Chemistry, University of Edinburgh, David Brewster Road, Edinburgh, EH9 3FJ (UK).
Helen S
HS
Niblock
EaStCHEM School of Chemistry, University of Edinburgh, David Brewster Road, Edinburgh, EH9 3FJ (UK). Alison.Hulme@ed.ac.uk.
Alison N
AN
Hulme
D000480:Alkynes / Q000737:chemistry*; D001688:Biological Products / Q000138:chemical synthesis / Q000737:chemistry; D003500:Cyclization; D019281:Dimerization; D018942:Macrolides / Q000138:chemical synthesis / Q000737:chemistry*; D010080:Oxazoles / Q000138:chemical synthesis / Q000737:chemistry*; D013237:Stereoisomerism
D000480:Alkynes; D001688:Biological Products; D018942:Macrolides; D010080:Oxazoles; C436383:disorazole C1
alkyne metathesis; cytotoxicity; natural products; self-assembly; total synthesis