115369-27-2Relevant academic research and scientific papers
Unified Synthesis of 10-Oxygenated Lycopodium Alkaloids: Impact of C10-Stereochemistry on Reactivity
Saha, Mrinmoy,Li, Xin,Collett, Nathan D.,Carter, Rich G.
, p. 5963 - 5980 (2016/07/23)
The pronounced impact of the C10 stereochemistry on the successful construction of a polycyclic Lycopodium alkaloid scaffold has been explored. A wide range of reaction conditions and functionality were investigated to control a keto sulfone Michael addition to construct the C7-C12 linkage. An unexpected, overriding impact of the C10 stereochemistry in stereoselectivity and reaction rate in the Michael addition was observed. Furthermore, divergent reactivity of a conformationally accelerated, intramolecular Mannich cyclization based on the C10 stereochemistry was discovered. The successful execution of this synthetic route resulted in the total synthesis of all three known 10-oxygenated Lycopodium alkaloids: 10-hydroxylycopodine, paniculine, and deacetylpaniculine.
Diastereoselective synthesis of tetrahydrofurans via reaction of γ,δ-epoxycarbanions with aldehydes
Makosza, Mieczyslaw,Barbasiewicz, Michal,Krajewski, Dariusz
, p. 2945 - 2948 (2007/10/03)
(Chemical Equation Presented) Hydroxymethyl-substituted tetrahydrofurans were prepared with high diastereoselectivity by reaction of the carbanion derived from 3,4-epoxybutyl phenyl sulfone with aldehydes in the presence of a mixture of lithium and potass
Chiral non-racemic dihydroxysulfones via hydrolytic kinetic resolutions - Synthesis of oxacyclic ring systems using intramolecular acylation strategies
Jin, Chunyang,Ramirez, Raina D.,Gopalan, Aravamudan S.
, p. 4747 - 4750 (2007/10/03)
A number of chiral non-racemic 1,2-dihydroxysulfones have been prepared in good yields and high enantiomeric excesses by hydrolytic kinetic resolution of the corresponding epoxysulfones with Jacobsen's (S,S)-salen(Co)III(OAc) catalyst. The intramolecular cyclization reactions of the acyl and ethoxycarbonyl derivatives of these dihydroxysulfones have been exploited to access a variety of functionalized chiral non-racemic cyclic ethers and lactones in good yields.
SYNTHESIS OF A MARINE POLYETHER TOXIN, OKADAIC ACID (2) -- SYNTHESIS OF SEGMENT B
Ichikawa, Yoshiyasu,Isobe, Minoru,Goto, Toshio
, p. 4749 - 4758 (2007/10/02)
The central synthetic segment B for okadaic acid comprises the carbons from 15 through 27 including 6 asymmetric carbons.Its synthesis started from a D-glucose derivative, whose carbon was extended twice for the six and five membered etherial ring formati
