110370-82-6Relevant articles and documents
A concise synthesis of (-)-aplyviolene facilitated by a strategic tertiary radical conjugate addition
Schnermann, Martin J.,Overman, Larry E.
, p. 9576 - 9580,5 (2012)
A second-generation synthesis of the rearranged spongian diterpene aplyviolene is reported. The key step is the addition of a trialkyl tertiary radical generated by photoredox-mediated fragmentation of a N-(acyloxy) phthalimide to an α-chloropentenone (se
Synthesis of the proposed structure of mucoxin via regio- and stereoselective tetrahydrofuran ring-forming strategies
Narayan, Radha S.,Borhan, Babak
, p. 1416 - 1429 (2007/10/03)
An enantioselective total synthesis of the proposed structure of mucoxin (1) is described. Mucoxin, an annonaceous acetogenin isolated from bioactive leaf extracts of Rollinia mucosa, is the first acetogenin containing a hydroxylated trisubstituted tetrah
Samarium(II) iodide-mediated reductive annulations of ketones bearing a distal vinyl epoxide moiety
Molander, Gary A.,Shakya, Sagar R.
, p. 5885 - 5894 (2007/10/03)
Samarium(II) iodide in the presence of hexamethylphosphoramide (HMPA) efficiently promotes the intramolecular coupling of ketones with distal epoxy olefins. The reaction appears to proceed by a mechanism wherein a ketyl couples with the unsaturated epoxide. Subsequent fragmentation of the epoxide ring in compounds 1a-k yields carbocycles 2a-k with an allyl alcohol side chain in good yields, and often with high diastereoselectivity. When tetramethylguanidine was used as an additive instead of HMPA, the desired carbocycle was obtained in good yield, but the diastereoselectivity was diminished. A palladium(0)-catalyzed SmI2 reaction provided the expected product in modest yield, but the sense of diastereoselectivity was reversed. In the latter case, a different reaction mechanism may be involved. Thus, formation of an allylsamarium species may be invoked, with nucleophilic carbonyl addition leading to the observed facial selectivity.
