Natural Product Synthesis

My group has been extensively involved in the synthesis of structurally novel, biologically active natural products.  We have focused on short and efficient routes that use new chemistry for the practical preparation of these targets.  Recently completed targets include 7-hydroxylycopodine, 291 phantasmidine,286 isotuberculosinol and tuberculosinol,282  maldoxin and maldoxone,289 berkeleic acid,272,275 vibralactone,270 chaetominine,268 platensimycin,264 polygalolides A and B,263 symbioimine,260 jenamidines A1/A2,259 thallusin,258 and SCH-642305.255

Other syntheses include epohelmins A and B,250 and Ficusceptine, juliprosine, and Juliprosopine.246 cladybotryal,241 TAN=2483A and waol A,234 ent-haterumalide NA,232 guanacastepene A,225 fumiquinazolines A, B, C, E, H, and I,224 martinellic acid,219 dysibetaine,217 salicylihalamide A,216 pyrinodemins A and B,210 TAN1251A-D,202 dysiherbaine,201 and FR901483,198

Earlier syntheses include asperlicin183 allocyathin B2 and erinacine A,182 cylindricines A, D, and E.177 rhopaloic acid,175 leporin A,167  chondrillin and plakorin,137 reiswigin A and B,122  and compactin.60

We have had a long standing interest in guanidine-containing natural products and have prepared phidianidines A and B,292 eusynstyelamide A,281 bistellettadine A,279 monanchorin,273 7-epineoptilocaulin, mirabilin, and isoptilocaulin,271  phloedictine A1,227 cylindrospermopsin,203 anchinopeptolide D,199 batzelladine E,184 the pentacyclic nucleus of ptilomycalin A,155 crambines A-C,149 and ptilocualin.77

Our oxidative free-radical cyclization studies with Mn(OAc)3 led to syntheses of isosteviol,191 gymnomitral,177 upial,166 methyl cantabradienate,158 avenaciolide,150  okicenone,147 velloziolone.144 and  podocarpic acid 86,153

Our intramolecular ketene cycloaddition studies led to synthesis of chyrsanthenone, β-cis and β-trans-bergamotenes, β-ylangene and β-copaene100,112 and methyl jasmonate.106

Our work with Lewis acid catalyzed ene and related reactions has led to syntheses of pseudomonic acid71 and numerous pheromones.