10236-06-3Relevant articles and documents
Stereocontrolled synthesis of 1,3,5-triols by an iteration of asymmetric dihydroxylation and deoxygenation
Walleser, Patrick,Brueckner, Reinhard
experimental part, p. 4802 - 4822 (2010/10/20)
Asymmetrie dihydroxylation of the Cγ=Cδ bonds in trans-configured α, β, γ, δ-unsaturated esters, carbonate formation, and Pd°-catalyzed deoxygenation of Cγ provided α, β-unsaturated δ-hydroxy esters. Protection and chain-extension provided the corresponding α, β-unsaturated ketones. Their asymmetric dihydroxylation in the presence of phenylboronic acid delivered dioxaborolanes. SmBr2-mediated deoxygenation of Ca, followed by Narasaka-Prasad and Claisen-Tishchenko reductions, respectively, selectively provided monoprotected 1,3syn, 3,5syn-, 1,3syn, 3,5anti-, 1,3anti, 3.5syn-, and 1,3anti, 3,5anticonfigured 1,3,5-triols. Enones with a bulky OSiR3 group at Cδ were dihydroxylated with significantly poorer syn (vs. anti) selectivities. Dominating reagent control modulated by opposing ( mismatched case ) or enhancing ( matched case ) substrate control, respectively, might be responsible.
The Synthesis of Two Furan-Based Analogues of the α′,β ′-Epoxy Ketone Proteasome Inhibitor Eponemycin
Bennacer, Bibia,Trubuil, Dominique,Rivalle, Christian,Grierson, David S.
, p. 4561 - 4568 (2007/10/03)
Myers's methodology for enantioselective amino acid synthesis was employed to prepare the N-Boc didehydroleucine amide derivative 15 and to effect its conversion into the acylfuran intermediate 17. Coupling of 19 (R = H) with N-(isooctanoyl)serine provided the furan-based analogue 4 of eponemycin (de = 96 %), a peptide epoxide with potent cytotoxic and anti-angiogenesis properties. In an identical fashion the corresponding unsaturated analogue 5 of eponemycin was prepared (de = 48%). Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003.
Synthesis of functionalized bicycloocta-2,6-dienes by thermal rearrangement of substituted 6-exo-(1-alkenyl)bicyclohex-2-ene systems
Piers, Edward,Jung, Grace L.,Ruediger, Edward H.
, p. 670 - 682 (2007/10/02)
Thermolysis of each of the enol silyl ethers 31-35 affords, cleanly and efficiently, the bicyclooctadienes 36-40, respectively.Similarly, thermal rearrangement of the enol silyl ether 50 provides the diene 51.Hydrolysis of 36, 37, and 39, and decar
