Fundamentals of Medicinal Chemistry

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10 An Introduction to Lead and Analogue Syntheses 10.1 Introduction Once the structure of a lead has been decided it is necessar ...

O HO O (iii) H+or OH− (ii) CrO 3 (iv) H 2 /Pd O CH 3 COO (i) CH 3 COOCOCH 3 Diosgenin Pregnenolone ethanoate Oestrogens Androgen ...

readily available. Thedisconnectionapproach (see section 10.3.1) may be used both to identify these starting materials and to de ...

ClCOC(CH 3 ) 3 NHCOCH 2 Ph NHCOCH 2 CH 2 CH 2 OCH 2 CH 3 NHCOC(CH 3 ) 3 ClCOCH 2 Ph ClCOCH 2 CH 2 CH 2 OCH 2 CH 3 NH 2 Figure 10 ...

Pure enantiomer e.g. (+)B isomer Two Isomers: [(+)A−(+)B] and [(−)A−(+)B] Diastereoisomers Pure (+)A−(+)B Pure (−)A−(+)B Pure (+ ...

e:e:or d:e:¼ ( yield of the major stereoisomeryield of the minor stereoisomer) yield of the major stereoisomerþyield of the min ...

Overall reaction: (a) Overall reaction: (b) CH 3 CH=CHCH 3 but-2-ene but-2-ene CH 3 CH=CHCH 3 OsO 4 /H 2 O CH 3 CHOHCHOHCH 3 (±) ...

discussed under the broad headings of either reactions that require a catalyst or those that do not require a catalyst for their ...

HO H +N H CF 3 Br− Cl O Cl CH 3 O CH 3 Cl/PhCH 3 /NaOH Cl O Cl H CH 3 O CH^3 (1) This starting compound is produced in the form ...

COOH HOOC CH 3 CH^3 H 2 N H 2 N H COCl 2 HN O O CH 3 O HN H N O H HOOC H H L-Proline Ph Ph Ph COOC 2 H 5 O N C C 2 H 5 OOC CH 3 ...

CH 2 OH N CO H H H HOOC C C NH NH H COOH LiAlH 4 H CH 2 OH (C 2 H 5 CO) 2 O N−− COCH 2 CH 3 H CH 2 OH S-(−)-Proline The chiral a ...

diastereoisomers are formed, the usefulness of the reaction will also depend on the ease of separation of these mixtures into th ...

Table 10.2 Examples of books and databases that catalogue chemical reactions Title Author Classification used Books: Synthetic O ...

those that give rise to either a stable species or occur by a feasible disconnection mechanism, such as hydrolysis, because the ...

Reduction Oxidation FGI FGI H 2 N CH 3 O 2 NO 2 N C C O O OH OH The final stage is to consider the disconnection of both the met ...

Table 10.3 Examples of most useful disconnections and reconnection systems. The compounds used for the reconnection reactions ar ...

Friedel-Crafts disconnections: Ar = an aromatic system. The position of substitution will depend on the nature of the substituen ...

Table 10.4 Examples of reactions used to reverse FGIs. R can be both an aromatic and an aliphatic residue but Ar is only an arom ...

(continued) (5) Explain the meaning of the term ‘synthon’. Draw the best synthons and their corresponding real compounds for eac ...