Bioactive natural products. / Part L by Atta-ur- Rahman

By Atta-ur- Rahman

Traditional Product Chemistry keeps to extend to fascinating new frontiers of significant significance in medication. Written through foreign experts in a number of fields of ordinary product chemistry, this most modern quantity within the well-established sequence Studies in normal items Chemistry comprises 23 chapters, overlaying issues starting from immunosuppressant and antimalarial compounds to bioactive ingredients valuable in melanoma and neural ailments. This current quantity, will back be of serious curiosity to investigate scientists and students operating within the interesting box of recent drug discovery.

* Written by means of foreign specialists within the a number of fields of average product chemistry
* includes 23 complete articles masking issues starting from immunosuppressant and antimalarial compounds to bioactive components beneficial in melanoma and neural diseases
* helpful resource of data for examine scientists and students within the box of recent drug discovery

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TsCI, DMAP, Et3N 3. 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).

When 43 in THF was treated with pyrrolidine and AcOH, the equatorial C(7) epimer of 44 was formed in 51% as the main product. 21 Owing to its rigid and concave architecture, hydroxyketone 44 was converted into diol 47 in a completely diastereoselective fashion by hydrogenation. To achieve a synthesis of 1 from 47, inversion of stereochemistry at C(9) and production of a C(9) monophosphate ester were required. It was possible to accomplish both objectives in a single step by a Mitsunobu reaction between 47 and dibenzyl hydrogen phosphate [37].

13 O2Me EtO2C,, T9 O,Me NH 2 NHOH Ss/Nk^--Ar / \ T | ] CO2Me 1. anisaldehyde OMe 2. HCI , (86%) 2. (77%) (73%) Ar 45psi H2, Pd/C, AcOH 1-TsCI ^ CO2Me . NaN3 (78%) \ < j S " Af f ]I I CO2Me O X n 23 Ar = p-OMeC6H4 1. 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.

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