Total synthesis of (+)-dactylolide.
[reaction: see text] The total synthesis of the new cytotoxic marine macrolide (+)-dactylolide (1) has been achieved in nine steps from known vinyl bromide (-)-AB. In addition, (+)-zampanolide (2) has been converted to (+)-dactylolide (1) via thermolysis.
Smith
Amos B
AB
Department of Chemistry, Monell Chemical Senses Center, and Laboratory for Research on the Structure of Matter, University of Pennsylvania, Philadelphia, Pennsylvania 19104, USA. smithab@sas.upenn.edu
Safonov
Igor G
IG
D000818:Animals; D000970:Antineoplastic Agents / Q000138:chemical synthesis*; D019086:Bridged Bicyclo Compounds, Heterocyclic / Q000138:chemical synthesis*; D007202:Indicators and Reagents; D007783:Lactones / Q000138:chemical synthesis*; D018942:Macrolides / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D013058:Mass Spectrometry; D011161:Porifera / Q000737:chemistry*
D000970:Antineoplastic Agents; D019086:Bridged Bicyclo Compounds, Heterocyclic; D007202:Indicators and Reagents; D007783:Lactones; D018942:Macrolides; C451487:dactylolide; C444900:zampanolide