Stereoselective synthesis of (−)-jimenezin

Organocatalyzed Glycosylation Reactions of Carbohydrates

“…The same high diastereoselectivities and high E/Z-ratios were detected in both series, using D-ribose 29 as The intermolecular addition of alcohols to terminal and activated alkynes has been reported before [133][134][135][136][137][138] and has been used extensively in radical cyclization of β-alkoxyacrylates [139][140][141][142][143][144][145][146][147][148][149][150][151][152][153][154], in reductive cyclizations of β-alkoxyacrylates (Maitotoxin total synthesis [155][156][157][158][159]) and palladium-catalyzed cyclization in the presence of CO [160]. For an overview of the application of alkynes in organocatalysis see reference [161].…”

Transition metals in organic synthesis: Highlights for the year 2005

“…Carbon-carbon double bond or triple bond reduction using Wilkinson's catalyst were used in synthesis of 10-hydroxyasimicin [323], murisolins [324], tuberostemonines [688], eupomatilones [211], guanacastepene A [942], pyragonicin [943], mucocin [944], 3-hydroxy-4-methyl-2-tetradecyl-4-butenolide [945], gleenol and axeenol [946], (−)-jimenezin [947], epi-(+)-SCH-642305 [948], methionine aminopeptidase-2-inhibitor [949] and the tricyclic core of cyathin diterpenoids [455]. Crabtree's iridium catalyst was used in synthesis of prodigiosines [198], batzelladine alkaloids (Eq.…”

Recent progress on the total synthesis of acetogenins from Annonaceae

“…In 2005, Lee’s group reported the total synthesis of jimenezin ( 426b ) via radical cyclization of β-alkoxyacrylate and β-alkoxyvinyl sulfoxide intermediates and intramolecular olefin metathesis reaction ( Scheme 62 ) [ 137 ]. Hydroxy oxane 434 was prepared from a β-alkoxyacrylate aldehyde precursor 433 via samarium(II) iodide-mediated cyclization.…”