A novel synthesis of (.+-.)-perhydrohistrionicotoxin

ChemInform Abstract: An Improved Method for the endo‐Fusion of Five‐Membered Ring Lactones to the Bornane Ring System.

“…Due to steric reasons (unhindered attack of hydride from the endo side of the bornane ring system) exo isomer 7 gave almost exclusively exo-lactone 9, whereas 2 yielded 3 and 4 in a ratio of just 55:40 only (see Scheme 1). When treated with allyltributylstannane [18] 5 gave C-allylated lactone 10 as sole product which is a promising starting mate-atom [10] . Time dependence of the ratio 5/6 from 3 by recrystallization.…”

Enantioselective Radical Reactions

“…The most common trap for a radical popularized by Keck is allyltributylstannane [139]. Porter et al performed the trapping of acyl radicals obtained from α-bromo oxazolidinones 178 with allylstannanes and allylsilanes (Scheme 47) [140].…”

An Improved Method for theendo-Fusion of Five-Membered Ring Lactones to the Bornane Ring System

“…Thus, no Finally, the reactivity of pseudoacid chloride 5 towards another stannane and two amines was investigated. When treated with allyltributylstannane [18] 5 gave C-allylated lactone 10 as sole product which is a promising starting mateatom [10] . But so far, from the analysis of the investigated substrates we could not rule out that the reaction takes rial for further functionalized derivatives of lactol 1 (Scheme 2).…”