By E. J. Corey, Xue-Min Cheng

ISBN-10: 0471115940

ISBN-13: 9780471115946

The good judgment of Chemical Synthesis The name of this three-part quantity derives from a key subject of the book-the common sense underlying the rational research of advanced artificial difficulties. even though the e-book offers nearly completely with molecules of organic foundation, that are excellent for constructing the elemental rules of multistep man made layout due to their architectural complexity and diversity, the strategy taken is absolutely acceptable to different varieties of carbon-based constructions. half One outlines the fundamental recommendations of retrosynthetic research and the final thoughts for producing attainable artificial pathways through logical aid of molecular complexity. Systematic retrosynthetic research and the concurrent use of a number of self sustaining thoughts to steer challenge fixing tremendously simplify the duty of devising a brand new synthesis. this manner of pondering has been used for greater than twenty years by means of one of many authors to educate the research of adverse artificial difficulties to many countless numbers of chemists. a considerable fraction of the problematic syntheses that have seemed within the literature in recent times were produced via those contributors and their scholars. half , a set of multistep syntheses, presents a lot built-in info on man made tools and pathways for the development of attention-grabbing aim molecules. those syntheses are the results of artificial making plans which used to be according to the overall rules summarized partly One. therefore, half serves to complement half One with emphasis at the reactions of synthesis and on particular examples of retrosynthetically deliberate syntheses. half 3 is meant to stability the insurance of components One and and to function a handy advisor to the now huge, immense literature of multistep synthesis. info on greater than 600 fascinating multistep syntheses of biologically derived molecules is integrated. it really is was hoping that the structural diversity and diversity of goal molecules offered partially 3 will attract many chemists.

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7 Retrosynthetic Analysis of Squalene (57) Squalene (57) (Chart 8) is important as the biogenetic precursor of steroids and triterpenoids. Its structure contains as complicating elements six trisubstituted olefinic linkages, four of which are Estereocenters. Retrosynthetic analysis of 57 can be carried out under T-goal guidance by selecting transforms which are both C-C disconnective and stereocontrolled. The appropriate disconnective Tgoals must contain in the retron the E-trisubstituted olefinic linkage.

The synthetic conversion of 70 to 69 is clearly a favored pathway, which makes 70 a valid intermediate. The Sharpless oxidation transform converts 70 to 71. Intermediate 71 can be converted retrosynthetically in a few steps via 72 to 73, which contains the Sharpless oxidation retron, and a 2-carbon, nucleophile such as 74 (protection/deprotection required). Application of the AE (KR) transform to 73 produces the readily available (±) alcohol 75. Alternatively the chiral from of 75 might be obtained by enantioselective reduction of 76 and then converted by an AE process to the required 73.

G. O, N, S, P) which are easily generated synthetically are strategic for disconnection. Specific bonds in this category are ester, amide, imine, thioether, and acetal. 4. g. C6H5CH2CH2CH2CH2 rather than simply C6H5 (this is essentially a special case of rule 1, above). 5. e. rings within chains) into molecular segments is frequently best accomplished by acyclic bond disconnection, especially when such rings are separated by one or more chain members. e. exo) to a ring, or 1, 2, or 3 bonds removed from it, depending on the type of ring which is involved.

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The Logic of Chemical Synthesis by E. J. Corey, Xue-Min Cheng

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