By Atta-ur- Rahman

ISBN-10: 0080458475

ISBN-13: 9780080458472

ISBN-10: 0444521712

ISBN-13: 9780444521712

Typical Product Chemistry maintains to extend to intriguing new frontiers of significant value in drugs. Written via overseas specialists in a number of fields of typical product chemistry, this most up-to-date quantity within the well-established sequence stories in normal items Chemistry comprises 23 chapters, protecting issues starting from immunosuppressant and antimalarial compounds to bioactive components important in melanoma and neural illnesses. This current quantity, will back be of significant curiosity to investigate scientists and students operating within the interesting box of recent drug discovery. * Written by means of overseas specialists within the numerous fields of common product chemistry* comprises 23 complete articles overlaying subject matters starting from immunosuppressant and antimalarial compounds to bioactive components beneficial in melanoma and neural ailments* worthy resource of knowledge for learn scientists and students within the box of recent drug discovery

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Extra resources for Bioactive Natural Products Part L

Example text

NaN3, DMF (79%) 2. ACOH (68%) O"3 Ar = p-OHC6H4 y,^Y—-Ar [ J CO2Me O ^^ / 134 Ar = p-OprenylC6H4 Me" LiAIH4 2. HCO2Ac 3. LiAIH4 (58%) TFAA, Et3N, POCF, CH2OH o 136 135 K2CO3, MeOH/H2O (60% from 135) f 129 (+)-TAN1251C(4) Scheme 40. Snider's synthesis of (+)-TAN125lC The synthesis starts from the N-Boc-tyrosine methyl ester, which was Obenzylated, since the prenyl ether required in the target compound is not compatible with the conditions required for the preparation of the hydoxylamine or the hydrogenation of the isoxazolidine intermediate (Scheme 40).

LiBH 4 , THF 2. HCI, AcOH, H2O (97%) N(Boc)Me 3. Boc2O, Et3N (95%) 4. Dess Martin 2. TFA, CH 2 CI 2 6 (PG = Boc) OMe OMe NHMe 25 (36%) OMe NHMe 26 (16%) 27 (5%) Scheme 10. Preparation of ketoaldehyde 6 and its aldol reaction UBH4 followed by an acid hydrolysis gave a deprotected keto alcohol, in which the secondary amine was again protected with BOC2O. Finally, the aldehyde intermediate 6 was obtained using the Dess Martin reagent. The aldol reaction of 6 proceeded analogously to that of the model ketoaldehyde 12, although in lower yield.

Ac2O, Py (41 %) lyie TPAP, NMO first generation <^N ^ (77%) ' 1. Ac2O, Py 2. L- Selectride NaOMe, 90%aq MeOH ~ UMU Y (44%) O 6 (PG=Ts) second generation 1. LiAIH4 (53 %) 59 2. (BnO)2PO2H, (C6H4CI)3P, DIAD, then Et3N 3. HCI •l< Cbz (29 %) OPO(OBn)2 Scheme 22. Ciufolini's synthesis of (-)-FR901483 58 (94%) 25 This somewhat surprising stereochemical result is attributable to the greater reactivity, and hence the lower selectivity, of LAH relative to other reducing agents. Working with alcohol 59 and its epimer at C(9), the Mitsunobu process leads to phosphate 58, as the major product, after conversion of the resulting extremely polar compounds to their iV-Cbz derivatives.

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