Total synthesis of (−)-microcarpalide from d-mannitol

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 …”

Gold(III) Chloride and Phenylacetylene: A Catalyst System for the Ferrier Rearrangement, and O‐Glycosylation of 1‐O‐Acetyl Sugars as Glycosyl Donors

“…These preliminary results led us to investigate the Ferrier rearrangement of 1 with sulfur, carbon, and nitrogen nucleophiles (Table 1, entries [11][12][13][14][15] to check the versatility of this catalyst system. The reaction of 1 with thiophenol (13) [27] proceeded smoothly to form thioglycoside 28 in 93 % yield within 5 min (Table 1, entry 11).…”

“…[9] 2-Acetoxymethyl glycals are wellknown synthons that undergo a Ferrier-rearrangement-type reaction to form C-2-methylene-substituted O-glycosides in the presence of catalysts such as BF 3 ·OEt 2 , [10] Nafion-H, Montmorillonite K-10, and LiClO 4 , [11] and InCl 3 . [12] More recently, AuCl 3 [13] has been reported as a catalyst for the Ferrier-like rearrangement of C-2-propargyloxymethyl glycals, where the propargyloxy group forms a leaving group by coordination with the Au III species.…”

Synthetic Studies of Natural 10-Membered Lactones, Mueggelone, Microcarpalide, and Sch 642305, Which Have Interesting Bioactivities

“…Interestingly, compared with Marco's synthesis, 22) E/Z selectivity at the ring-closing step was greatly improved by changing the protective groups. Similarly, Ghosh et al also reported a total synthesis of microcarpalide using the same precursor 24 for RCM in 2005, 34) in which all four stereocenters were derived from D-mannitol (scheme not shown). [3]).…”