Stereocontrolled synthesis of the diene and triene macrolactones of oximidines I and II: organometallic coupling versus standard macrolactonization.
[structure: see text]. Stereocontrolled construction of the 12-membered diene and triene lactones 1, 2, and 3, characteristic of the antitumor agent oximidines I and II, are reported and were based on an intramolecular Castro-Stephens coupling for the construction of a cyclic enyne or dienyne followed by stereoselective reduction of the cyclic alkyne for introduction of the cis-olefin of the targets. A comparison of the effectiveness of this protocol is made with standard macrolactonization.
Coleman
R S
RS
Department of Chemistry, The Ohio State University, 100 West 18th Avenue, Columbus, Ohio 43210, USA. coleman@chemistry.ohio-state.edu
Garg
R
R
D000970:Antineoplastic Agents / Q000138:chemical synthesis* / Q000737:chemistry; D003500:Cyclization; D007202:Indicators and Reagents; D007783:Lactones / Q000138:chemical synthesis* / Q000737:chemistry; D008958:Models, Molecular; D009942:Organometallic Compounds / Q000737:chemistry*; D018036:Selenium Compounds / Q000138:chemical synthesis*; D013237:Stereoisomerism
D000970:Antineoplastic Agents; D007202:Indicators and Reagents; D007783:Lactones; D009942:Organometallic Compounds; D018036:Selenium Compounds; C442269:selenecic acid; C442270:selenol