59096-18-3Relevant articles and documents
Concise Total Syntheses of (±)-Joubertiamine, (±)- O -Methyljoubertiamine, (±)-3′-Methoxy-4′- O -methyljoubertiamine, (±)-Mesembrane, and (±)-Crinane
Das, Mrinal Kanti,De, Subhadip,Bisai, Alakesh
, p. 2093 - 2104 (2016/07/06)
A method to access cis-3a-aryloctahydroindole alkaloids has been developed through a key strategy involving Eschenmoser-Claisen rearrangement of allylalcohol. This approach gives us an opportunity to access the all-carbon quaternary center required for ci
Asymmetric Synthesis Using Chiral Acetals: Highly Stereoselective Reduction of Chiral α-Keto-β,γ-unsaturated Acetals and Its Application for the Synthesis of (R)-(-)- and (S)-(+)-3'-Methoxy-4'-O-methyljoubertiamine
Fujioka, Hiromichi,Annoura, Hirokazu,Murano, Kenji,Kita, Yasuyuki,Tamura, Yasumitsu
, p. 2047 - 2052 (2007/10/02)
Reduction of the chiral α-keto-β,γ-unsaturated acetals (1) derived from (-)-(2S,3S)-1,4-dimethoxy-2,3-butanediol was studied.Extremily high stereoselectivity was attained with LiAlH4 and two epimeric allyl alcohols (2aA-2cA and 2aB-2cB) were prepared selectively by a proper choice of additive.As an application of this methodology, total syntheses of (R)-(-)-3'-methoxy-4'-O-methyljoubertiamine and its enantiomer were achieved from the single chiral enone acetal (3) through a highly stereocontrolled reduction followed by the Claisen-Eschenmoser rearrangement.