{"refrec":{"BRefID":383479,"RR":"<b>Alexander, B.W.; Bartfield, N.M.; Gupta, V.; Mercado, B.Q.; Del Campo, M.; Herzon, S.B.</b> (2024). An oxidative photocyclization approach to the synthesis of <i>Securiflustra securifrons</i> alkaloids. <i>Science (Wash.) 383(6685)</i>: 849-854. <a href=\"https://dx.doi.org/10.1126/science.adl6163\" target=\"_blank\">https://dx.doi.org/10.1126/science.adl6163</a>","BEntID":381225,"PublicFlag":1,"CheckedFlag":0,"wosflag":1,"vabbflag":1,"RefStringPartII":". <i>Science (Wash.) 383(6685)</i>: 849-854. <a href=\"https://dx.doi.org/10.1126/science.adl6163\" target=\"_blank\">https://dx.doi.org/10.1126/science.adl6163</a>","DocTypID":8,"DocType":"Journal article","MarineFlag":1,"FreshFlag":0,"BrackishFlag":0,"TerrestrialFlag":0,"Authorstring":"Alexander, B.W.; Bartfield, N.M.; Gupta, V.; Mercado, B.Q.; Del Campo, M.; Herzon, S.B.","OrigTitleTranslFlag":0,"Authorstringtrunc":"Alexander, B.W. <i>et al.</i>","Englishabstract":"Securines and securamines are cytotoxic alkaloids that contain reactive alkene and heterocyclic residues embedded in skeletons comprising four to six oxidized rings. This structural complexity imparts a rich chemistry to the isolates but has impeded synthetic access to the structures in the nearly three decades since their isolation. We present a flexible route to eight isolates that exemplify the three skeletal classes of metabolites. The route proceeds by the modular assembly of the advanced azides 38 and 49 (13 steps, 6 to 10% yield), sequential oxidative photocyclizations, and late-stage functional group manipulations. With this approach, the targets were obtained in 17 to 19 steps, 12 to 13 purifications, and 0.5 to 3.5% overall yield. The structure of an advanced intermediate was elucidated by microcrystal electron diffraction (MicroED) analysis. 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