专利号:US-8222458-B2 优先权日:2008-06-13 标题 :Process or synthesis of (3S)- and (3R)-3-hydroxy-beta-ionone, and their transformation to zeaxanthin and beta-cryptoxanthin 发明人:KHACHIK FREDERICK; CHANG AN-NI 权利人:KHACHIK FREDERICK; CHANG AN-NI; UNIV MARYLAND 摘要:Disclosed is a process for the synthesis of (3R)-3-hydroxy-β-ionone and its (3S)-enantiomer in high optical purity from commercially available (rac)-α-ionone. The key intermediate for the synthesis of these hydroxyionones is 3-keto-α-ionone ketal that was prepared from (rac)-α-ionone after protection of this ketone as a 1,3-dioxolane. Reduction of 3-keto-α-ionone ketal followed by deprotection, lead to 3-hydroxy-α-ionone that was transformed into (rac)-3-hydrox-β-ionone by base-catalyzed double bond isomerization in 46% overall yield from (rac)-α-ionone. The racemic mixture of these hydroxyionones was then resolved by enzyme-mediated acylation in 96% ee. (3R)-3-Hydroxy-β-ionone and its (3S)-enantiomer were respectively transformed to (3R)-3-hydroxy-(β-ionylideneethyl)triphenylphosphonium chloride [(3R)-C 15 -Wittig salt] and its (3S)-enantiomer [(3S)-C 15 -Wittig salt] according to known procedures. Double Wittig condensation of these Wittig salts with commercial available 2,5- dimethtylocta-2,4,6-triene-1,8-dial provided all 3 stereoisomers of zeaxanthin. Similarly, (3R)-C 15 -Wittig and its (3S)-enantiomer were each coupled with β-apo-12′-carotenal.
专利号:US-4322353-A 优先权日:1980-04-18 标题:Synthesis of dioxabicyclo(3.2.1)octanes and oxepanes 发明人:HAJOS ZOLTAN G; WACHTER MICHAEL P 权利人:ORTHO PHARMA CORP 摘要:The synthesis of C-4 alkyl homologs of racemic (1RS, 4SR,5RS)-4-(4,8-dimethyl-5-hydroxy-7-nonenyl)-4-methyl-3,8-dioxabicyclo[3.2.1]octane-1-acetic acid and the corresponding (1RS,4RS,5RS) - derivative is described. The dioxabicylo[3.2.1]octanes are useful as contragestational agents.
专利号:US-5597931-A 优先权日:1992-03-30 标 题:Total synthesis of taxol and analogues thereof 发明人:DANISHEFSKY SAMUEL J; MASTERS JOHN; YOUNG WENDY; LINK J THOMAS; ISAACS RICHARD; SNYDER LAWRENCE B 权利人:SLOAN KETTERING INST CANCER 摘要:The present invention provides three basic routes for the total synthesis of taxol having the structure: ##STR1## The present invention also provides the intermediates produced in the above processes, processes for synthesizing these intermediates as well as analogues of taxol and nortaxol.
专利号:US-4482730-A 优先权日:1981-09-24 标题:Synthesis of dioxabicyclo[3.2.1]octanes and oxepanes 发明人:HAJOS ZOLTAN G; WACHTER MICHAEL P 权利人:ORTHO PHARMA CORP 摘要:The synthesis of C-4 alkyl homologs of racemic (1RS,4SR,5RS)-4-(4,8-dimethyl-5-hydroxy-7-nonenyl)-4-methyl-3,8-dioxabicyclo[3.2.1]octane-1-acetic acid and the corresponding (1RS,4RS,5RS) - derivative is described. The dioxabicylo[3.2.1]octanes are useful as contragestational agents.
专利号:US-5488116-A 优先权日:1992-03-30 标 题:Total synthesis of taxol and analogues thereof 发明人:DANISHEFSKY SAMUEL J; BORNMANN WILLIAM G; QUENEAU YVES; MAGEE THOMAS V; KROL WALTER J; MASTERS JOHN J; JUNG DAVID K 权利人:SLOAN KETTERING INST CANCER 摘要:The present invention provides three basic routes for the total synthesis of taxol having the structure: ##STR1## The present invention also provides the intermediates produced in the above processes, processes for synthesizing these intermediates as well as analogues of taxol and nortaxol.
专利号:US-5527924-A 优先权日:1992-03-30 标题 :Total synthesis of taxol 发明人:DANISHEFSKY SAMUEL J; BORNMANN WILLIAM G; QUENEAU YVES; MAGEE THOMAS V; KROL WALTER J 权利人:SLOAN KETTERING INST CANCER 摘要:The present invention provides two basic routes for the total synthesis of taxol having the structure: The present invention also provides the intermediates produced in the above processes, processes for synthesizing these intermediates as well as analogs to taxol. Both the intermediates and analogs to taxol may prove to be valuable anticancer agents.