Reference

Application of the b-Ketoimide-Derived Dipropionyl Synthon to the Enantioselective Synthesis of the Macrolide Antibiotic Oleandolide

Application of the b-Ketoimide-Derived Dipropionyl Synthon to the Enantioselective Synthesis of the Macrolide Antibiotic Oleandolide. Evans, David A.; Kim, Annette S. 183960-62-5 and 131685-53-5 are cas registry numbers. These chemicals are also mentioned in this article. (Department of Chemistry, Harvard University, Cambridge, MA 02138, USA). Journal of the American Chemical Society, 118(45), 11323-11324 (English) 1996 American Chemical Society. CODEN: JACSAT. ISSN: 0002-7863. DOCUMENT TYPE: Journal CA Section: 26 (Biomolecules and Their Synthetic Analogs) Synthesis of oleandolide was completed in 18 linear steps with a 15% overall yield. Utilizing auxiliary-controlled aldol reactions, directed redns., and a directed epoxidn., the 10 stereocenters of oleandolide were established on the acyclic carbon framework from the chiral b-ketoimide building block (I). .

Synthesis of discodermolide and analogs

Florence, Gordon; Koch, Guido; Loiseleur, Olivier; Mickel, Stuart John; Paterson, Ian (Novartis Ag; Novartis Pharma Gmbh; Cambridge University Technical Services Ltd., Switz.). PCT Int. Appl. WO 2004009574 A1 29 Jan 2004, 113 pp. DESIGNATED STATES: W: AE, AG, AL, AM, AT, AU, AZ, BA, BB, BG, BR, BY, BZ, CA, CH, CN, CO, CR, CU, CZ, DE, DK, DM, DZ, EC, EE, ES, FI, GB, GD, GE, GH, HR, HU, ID, IL, IN, IS, JP, KE, KG, KP, KR, KZ, LC, LK, LT, LU, LV, MA, MD, MK, MN, MX, NI, NO, NZ, OM, PG, PH, PL, PT, RO, RU, SC, SE, SG, SK, SY, TJ, TM, TN, TR, TT, UA, US, UZ, VC, VN, YU, ZA, ZW, AM, AZ, BY, KG, KZ, MD, RU, TJ, TM; RW: AT, BE, CH, CY, DE, DK, ES, FI, FR, GB, GR, IE, IT, LU, MC, NL, PT, SE, TR. (English). (World Intellectual Property Organization). CODEN: PIXXD2. CLASS: ICM: C07D309-30. APPLICATION: WO 2003-EP7940 21 Jul 2003. PRIORITY: US 2002-PV397973 22 Jul 2002; GB 2002-23731 11 Oct 2002. DOCUMENT TYPE: Patent CA Section: 26 (Biomolecules and Their Synthetic Analogs) A process for prepg. discodermolide, its intermediates, and discodermolide analogs is presented. The process consists of prepg. triene I (R1, R2, R3, R4 = hydroxy protecting groups, where R1 and R4 can be split off without cleaving R2 or R3) from reacting vinyl compd. II with diene III (R3, R4 are different protecting groups, X = leaving group; R4 can be removed without affecting R3). In the next step of the syntheses, the protecting groups R1 and R4 are split off to give I (R1 = R4 = H, R2, R3 = identical or different hydroxy protecting groups). Then the only primary hydroxy group in I is selectively oxidized to provide an aldehyde. The aldehyde is reacted with a phosphonate ester to give a ketone IV (R2, R3 = identical or different hydroxy protecting groups, R4 = H) and optionally, the ketone is reacted with Cl3C(O)NCO to give IV (R4 = H2NCO). The aldol reaction of IV with an aldehyde provides the key triene I. 443761-69-1 and 131685-53-5 are just another two chemicals used in this study. I is then converted into discodermolide V (R2, R3, R5 = H, R4 = H2NCO) and its analogs V (R2, R3, R5 = identical or different hydroxy protecting groups). .