Solution‐ and Solid‐Phase Synthesis of Radicicol (Monorden) and Pochonin C

Abstract

A modular synthesis for pochonin C and radicicol is reported. The two natural products were prepared in seven and eight steps, respectively, from three readily available fragments. Alternative syntheses of these compounds were achieved using a combination of polymer-bound reagents and solid phase reactions. The conformation of the two natural products was studied and compared by using 2D NMR spectroscopy.

Transition metals in organic synthesis: Highlights for the year 2005

“…(221)) [1117,1118], hybrids of d-galactose with 1-deoxynojirimycin analogs [1119], the tetracyclic core of tetrapentalones [1120], 1-epi aglycon of cripowellins A and B [445], gambieric acid [1121], aspercyclide C [524], radicicol and pochonin C [1122], trachelanthamidine [1123], heliannuols G and H [652], (−)-Geismann-Waiss lactone [1124], tuberostemonines [688], (−)-kendomycin [1125], pochonin D [1126], (−)-223A [1127], coleophomones B-D [1128], brevetoxin B [130], garsubellin A [45], fostriecin [48], 11-acetoxy-4-deoxyasbestin D [1129], (+)-cyclophellitol [1130], ␤-C-glycosides [50], zoapatanol [247], deoxymannojirimycin and swainsonine [1131], valienamine [1132], A 3 adenosine recetor agonists [1133], vincantril [810], (−)-perhydrohistrionicotoxin [1134], annonaceous acetogenins [1135], deoxycombrestatin A-4 analogs [1136], (+)-lentiginosine and analogs [1137], N-malayamycin A [1138], (−)-salicylhalamides A and B [938], oxytocin analogs [1139], steroid-like compounds [440], (−)-isoprelaurefucin [338], halichondrin B [1140], (−)-microcarpalide and (+)-lethaloxin [1141,1142], anamarine …”

“…Alkene-alkene CM were used in synthesis toward viridiofungin A [1226], 2,7-diaminosuberic acid derivatives [1227], radicicol and pochonin C [1122], (+)-cyanthiwigin U [1228], apoptolidinone (Eq. (225)) [1229], the C9-C16 segment of ambruticin [1230], (−)-lemonomycin [1231], aureothin and Nacylaureothamine [61], the C22-C36 subunit of halichondrin B [654], the A ring of bryostatin analogs [1232], misakinolide A [1233], ␣-C-glucosyl serine and alanine [1234], the C26-C40 subunit of spirastrellolide [941], glutamic acid side chain homologues [1235], discodermolide analogues [1236], the C6-C21 segment of amphidinolide E [270], fraxinellone limonoids [1237], (+)-phomopsolide C [1167], pinnaic acid and halichlorine [1238], sphingosines [1239], mollugin and microphyllaquinone [1240], mucocin [645], (+)-anatoxin-a [1241], colletodiol [1242], toward paulitin [1243], tashiromine [1244], (−)-nupharamine [1245], octalactin lactone [1246], 3-hydroxy-4-methyl-2-tetradecyl-4-butenolide [945], 5,5-dimethylproline [1247], xenovenine and indolizine 209D [1248] and bengamides [1249].…”

Divergent Synthesis of a Pochonin Library Targeting HSP90 and In Vivo Efficacy of an Identified Inhibitor

“…It is important to note that this reaction sequence is not possible in the absence of the oxime functionality as it leads to the formation of coumarin. [32] The resins were then treated with the secondgeneration Grubbs catalyst under microwave irradiation to obtain the macrocycles 12 in excellent yield and purity after cleavage from the resin with hexafluoroisopropanol (HFIP). In contrast to TFA, these mild cleavage conditions were found to leave the EOM groups intact, thus enabling a subsequent selective esterification or amidation.…”

Spectroscopic and theoretical studies of some 2-substituted N-methoxy-N-methyl-amides

“…The 2-substituted-N-methoxy-N-methyl-amides [ZAC(O)N(OCH 3 )(CH 3 )] (Z = BrCH 2 1 [4], PhSeCH 2 4 [5]) have already been described in the literature. The 2-substituted-N-methoxy-N-methyl amides (Z = EtSCH 2 2 and Me 2 CSEt 3) are new compounds and were obtained as follows: initially the 2-ethylthio-acetic and 2-ethylthio-isobutyric acids were converted to the corresponding acyl chlorides through their reaction with thionyl chloride [6].…”