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Julia indole synthesis

Other examples of sigmatropic rearrangements leading to indoles are presented in the next chapter, or more appropriately elsewhere in this monograph. [Pg.137]

Indole Ring Synthesis From Natural Products to Drug Discovery, First Edition. Gordon W. Gribble. 2016 John Wiley Sons, Ltd. Published 2016 by John Wiley Sons, Ltd. [Pg.137]

Nucleophilic cyclization is a common tactic in all branches of organic chemistry, and several indole ring syntheses, which are presented in Chapters 8 through 22, employ this reaction as the central theme in the synthesis. The Sugasawa indole synthesis (Chapter 22) uses both nucleophilic and electrophilic reactions. [Pg.145]


Another category Ic indole synthesis involves cyclization of a-anilino aldehydes or ketones under the influence of protonic or Lewis acids. This corresponds to retro.synthetic path d in Scheme 4.1. Considerable work on such reactions was done in the early 1960s by Julia and co-workers. The most successful examples involved alkylation of anilines with y-haloacetoacetic esters or amides. For example, heating IV-substituted anilines with ethyl 4-bromoacetoacetate followed by cyclization w ith ZnClj gave indole-3-acetate esterfi]. Additional examples are given in Table 4.3. [Pg.41]

Julia s synthesis of lysergic acid 2 jj based on internal nucleophilic trapping of a benzyne intermediate in the ring C-seco intermediate (A). As in an earlier approach, the synthesis proceeds via indoline derivatives and formation of the indole nucleus is deferred until the very end. ... [Pg.158]

Spirotryprostatin A 142 and B 143 are two powerfully bioactive indole alkaloids. Both compounds inhibit the cell cycle in the G2/M phase, and 143 shows cytotoxic activity on the growth of human leukemia cell lines. Meyers and Carreira reported a total synthesis of 143. The Kocienski modified Julia olefmation was used in the formation of trisubstituted olefin without scrambling at Ci8. The alkene 146 was prepared in 78% yield by reacting sulfone 145 with aldehyde 144. The final product 143 was obtained by four-step reaction from the intermediate 146. [Pg.468]


See other pages where Julia indole synthesis is mentioned: [Pg.137]    [Pg.137]    [Pg.137]    [Pg.138]    [Pg.137]    [Pg.137]    [Pg.137]    [Pg.138]    [Pg.870]    [Pg.220]   
See also in sourсe #XX -- [ Pg.137 ]




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