zaragozic-acid-c and tartaric-acid

zaragozic-acid-c has been researched along with tartaric-acid* in 1 studies

Other Studies

1 other study(ies) available for zaragozic-acid-c and tartaric-acid

Article	Year
Total syntheses of zaragozic acids A and C by a carbonyl ylide cycloaddition strategy. Chemistry (Weinheim an der Bergstrasse, Germany), 2006, Dec-04, Volume: 12, Issue:35 A carbonyl ylide cycloaddition approach to the squalene synthase inhibitors zaragozic acids A and C is described. The carbonyl ylide precursor 8 was synthesized starting from di-tert-butyl D-tartrate (47) via an eleven-step sequence involving the regioselective reduction of the mono-MPM (MPM=4-methoxybenzyl) ether 48 with LiBH4 and the diastereoselective addition of sodium tert-butyl diazoacetate to alpha-keto ester 10. The reaction of alpha-diazo ester 8 with 3-butyn-2-one (40) in the presence of a catalytic amount of [Rh2(OAc)4] gave the desired cycloadduct 59 as a single diastereomer. The dihydroxylation of enone 59 followed by sequential transformations permitted the construction of the fully functionalized 2,8-dioxabicyclo[3.2.1]octane core 5. Alkene 79 derived from 5 serves as a common precursor to zaragozic acids A (1) and C (2), since the elongation of the C1 alkyl side chain can be attained by olefin cross-metathesis, especially under the influence of Blechert's catalyst (85). Topics: Alkenes; Bridged Bicyclo Compounds, Heterocyclic; Catalysis; Cross-Linking Reagents; Cyclization; Enzyme Inhibitors; Models, Chemical; Organometallic Compounds; Stereoisomerism; Tartrates; Tricarboxylic Acids	2006

Article

Year

Total syntheses of zaragozic acids A and C by a carbonyl ylide cycloaddition strategy.

Chemistry (Weinheim an der Bergstrasse, Germany), 2006, Dec-04, Volume: 12, Issue:35

A carbonyl ylide cycloaddition approach to the squalene synthase inhibitors zaragozic acids A and C is described. The carbonyl ylide precursor 8 was synthesized starting from di-tert-butyl D-tartrate (47) via an eleven-step sequence involving the regioselective reduction of the mono-MPM (MPM=4-methoxybenzyl) ether 48 with LiBH4 and the diastereoselective addition of sodium tert-butyl diazoacetate to alpha-keto ester 10. The reaction of alpha-diazo ester 8 with 3-butyn-2-one (40) in the presence of a catalytic amount of [Rh2(OAc)4] gave the desired cycloadduct 59 as a single diastereomer. The dihydroxylation of enone 59 followed by sequential transformations permitted the construction of the fully functionalized 2,8-dioxabicyclo[3.2.1]octane core 5. Alkene 79 derived from 5 serves as a common precursor to zaragozic acids A (1) and C (2), since the elongation of the C1 alkyl side chain can be attained by olefin cross-metathesis, especially under the influence of Blechert's catalyst (85).

Topics: Alkenes; Bridged Bicyclo Compounds, Heterocyclic; Catalysis; Cross-Linking Reagents; Cyclization; Enzyme Inhibitors; Models, Chemical; Organometallic Compounds; Stereoisomerism; Tartrates; Tricarboxylic Acids

2006