Synthetic Approaches and Total Synthesis of Natural Zoapatanol

Abstract

[structure: see text] The total synthesis of (+)-zoapatanol utilizing an intramolecular Horner-Wadsworth-Emmons olefination and an enantioselective Sharpless dihydroxylation as the key steps has been achieved. An advanced oxepene intermediate has been obtained by applying a ring-closing metathesis to an unsaturated enol ether.

Identification and Synthesis of the Male-Produced Sex Pheromone of the Soldier BeetleChauliognathus fallax(Coleoptera: Cantharidae)

“…In order to obtain synthetic samples of (1) to confirm the proposed structure and to perform field bioassays, a synthetic route started with Swern oxidation of undecan-1-ol (3) to undecanal (A) (92%), 13 followed by Wittig reaction between the ylide generated from the phosphonuim salt of 1-bromododecane (4) and undecanal in 86% yield (Scheme 1).…”

Transition metals in organic synthesis: Highlights for the year 2005

“…Intramolecular couplings were used in synthesis of isocomplestatin [244] and biphenomycin B [245]. (11) Alkyl boron reagents were used in synthesis of for example minfiensine [246], zoapatanol [247], dibenzocyclooctadiene lignans [248,249], the C1-C25 fragment of amphidinol 3 [250], (+)-SCH-351448 [251], the C10-C24 fragment of inostamycins [252], (+)-brefeldin C [253], (+)-wortmannin [254], cordiaquinone J and K [255] and cannabinoid antagonists [256].…”

“…A sequential asymmetric intramolecular Heck reaction-iminium ion cyclization was used in a synthesis of minfiensine (Eq. (34)) [247]. (34) A copper-catalyzed intermolecular Heck reaction in ionic liquids was developed [458].…”

“…Rhodium-catalyzed oxygen-hydrogen bond insertions were used in synthesis of (+)-zoapatanol [247], (−)-dihydroxanthatin [735] and (−)-xeniolide F [736].…”

“…(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 …”