1838-94-4Relevant articles and documents
PREPARATIVE SYNTHESIS OF ISOPRENE OXIDE
Arakelyan, A. S.,Dvoryanchikov, A. I.,Gevorkyan, A. A.
, p. 604 - 605 (1989)
The reaction of isoprene, hydrogen peroxide, and commercial hydrobromic acid gives 1-bromo-2-methyl-3-buten-2-ol, the low-temperature dehydrobromination of which gives isoprene oxide in high yield.
Enantioselective total synthesis of the reported structures of (-)-9-epi-presilphiperfolan-1-ol and (-)-presilphiperfolan-1-ol: Structural confirmation and reassignment and biosynthetic insights
Hong, Allen Y.,Stoltz, Brian M.
, p. 9674 - 9678,5 (2012)
When epi isn't. The first total synthesis of the reported structures of 9-epi-presilphiperfolan-1-ol and presilphiperfolan-1-ol has been achieved. Key steps are a catalytic asymmetric alkylation of a novel diene-containing electrophile followed by a two-carbon ring contraction and an intramolecular Diels-Alder cycloaddition to form the stereochemically dense tricyclic core. The synthetic work has resulted in the structural revision of presilphiperfolan-1- ol (see scheme). Copyright
Total synthesis and absolute configuration assignment of MRSA active garcinol and isogarcinol
Socolsky, Cecilia,Plietker, Bernd
, p. 3053 - 3061 (2015)
A short total synthesis of (±)-garcinol and (±)-isogarcinol, two endo-type B PPAPs with reported activity against methiciline resistant Staphylococcus aureus (MRSA), is presented. The separation of framework-constructing from framework-decorating steps and the application of two highly regio- and stereoselective Pd-catalysed allylations, that is, the Pd-catalysed decarboxylative Tsuji-Trost allylation and the diastereoselective Pd-catalysed allyl-allyl cross-coupling, are key elements that allowed the total synthesis to be accomplished within 13 steps starting from acetylacetone. After separation of the enantiomers the absolute configurations of the four natural products (i.e., (-)-garcinol, (+)-guttiferone E (i.e., ent-garcinol), (-)-isogarcinol, and (+)-isoxanthochymol (i.e., ent-isogarcinol)) were assigned based on ECD spectroscopy.
Synthetic studies on pseudolaric acid B: Enantioselective synthesis of C4,C10-di-epi-trans-fused [5-7]-bicyclic skeleton
Guo, Rui,Zhai, Hongbin,Li, Yun
, p. 1400 - 1402 (2021)
Studies on the synthesis of antifungal and anticancer natural product, pseudolaric acid B, have led to the enantioselective synthesis of di-epi-trans-fused [5–7]-bicyclic core skeleton. The synthesis was achieved in 10 linear steps, which features the Sharpless asymmetric epoxidation, cyanide-opening reaction of epoxide, and intramolecular [5 + 2] cycloaddition reaction as the key transformations. The stereochemistry was determined by the X-ray crystallographic analysis.
Regioselective Monoepoxidation of 1,3-Dienes Catalysed by Transition-metal Complexes
Thomsen, Dorte S.,Schioett, Birgit,Jorgensen, Karl Anker
, p. 1072 - 1074 (1992)
A procedure for regioselective monoepoxidation of mainly the less substituted double bond of 1,3-dienes with sodium hypochlorite or iodosylbenzene using various metal complexes as catalysts is presented; the results obtained are different from those found when applying the usual epoxidation reagents.
Enantioselective Radical-Polar Crossover Reactions of Indanonecarboxamides with Alkenes
Cao, Weidi,Feng, Xiaoming,Liu, Xiaohua,Wu, Wangbin,Xu, Xi,Yu, Han,Zhang, Xiying
supporting information, p. 4846 - 4850 (2020/02/11)
Highly efficient asymmetric intermolecular radical-polar crossover reactions were realized by combining a chiral N,N′-dioxide/NiII complex catalyst with Ag2O under mild reaction conditions. Various terminal alkenes and indanonecarboxamides/esters underwent radical addition/cyclization reactions to afford spiro-iminolactones and spirolactones with good to excellent yields (up to 99 %) and enantioselectivities (up to 97 % ee). Furthermore, a range of different radical-mediated oxidation/elimination or epoxide ring-opening products were obtained under mild reaction conditions. The Lewis acid catalysts exhibited excellent performance and precluded the strong background reaction.
