The Thesis Entitled “Synthetic Studies On Anthracyclinones, 1,4-Anthraquinones And Benzo[D]Naphtho[1,2-B]Pyran-6-Ones” Describes I) A Direct Synthetic Access To 1,4-Dihydroxyanthraquinones And Exploratory Studies Towards Anthracyclinones (E.G. 1) And A Synthesis Of Two Naturally Occurring 9,10-Anthraquinones Ventinone A (2) And 4-Methyl Ether Of Erythroglaucin (Also Proposed Structure Of Ventinone B) (3), Ii) Total Synthesis Of 9,10-Dimethoxy-2-Methyl-1,4-Anthraquinone (4) And Iii) Model Studies Towards Chrymutasins (5) And Gilvocarcins (8). The Key Reactions Investigated Are Hauser Annulation And Carbonyl-Ene Reaction. 1 : Idarubicinonedcbaoomeomeome4ooroch3nh2oabcedo5: Chrymutasin A, R = Fucose-- Digitalose6: Chrymutin, R = Hoohomeomeroohohohohme7: Gilvocarcin V, R = CH=CH28: Gilvocarcin M, R = CH3ABCOOOHOHOHOHOOOOHOHOR1MeOR2R32: Ventinone A, R1= H, R2= R3= Me3: 4-Methyl Ethr Of Erythroglaucin, R1= R2= Me, R3= H 3-Phenylsulfanylphthalides (E.G. 9) Readily React With P-Benzoquinones (E.G. 10) In The Presence Of T-Buoli In THF To Furnish 1,4-Dihydroxyanthraquinones (E.G. 11) In Good Yields And One-Pot Operations. This Methodology Has Been Applied To The Total Synthesis Of Naturally Occurring Anthraquinones, Ventinone A (2) And 4-Methyl Ether Of Erythroglaucin (3). Oosphoot-Buoli,60 Oc To R.T.R2R1R2OOOHOH 30-70%XXR1R1, R2 = Alkyl, O-Alkyl, -(CH2)4-, -(CH2)3CH(OH)-, -CH=CH-CH=CH-, Etc.15 Examples Have Been Worked Out91011 Key Words: Synthesis, Anthracyclinone, 1,4-Anthraquinone, Cyclopropaanthraquinone, Benzonaphthopyranone, Hauser Annulation, Intramolecular Carbonyl-Ene Reaction, Kochi-Anderson Radical Alkylation Reaction, Claisen Rearrangement, Heck Reaction.
Thesis Submitted To Indian Institute Of Technology, Kharagpur For The Award Of The Degree Of Doctor Of Philosophy By Sutapa Ray Under The Guidance Of Prof. Dipakranjan Mal DEPARTMENT OF CHEMISTRY INDIAN INSTITUTE OF TECHNOLOGY, KHARAGPUR SEPTEMBER 2008 © 2008, Sutapa Ray. All Rights Reserved.