adv_org_chem_13-2-6(2)
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The document summarizes the total synthesis of discodermolide, a very complex chainlike compound containing 13 stereocenters. It describes a novel aldol-based approach for the synthesis that uses a Lewis acid-induced addition of an allylic silane to an aldehyde as a key step. This approach is a hybrid of methods used by Novartis and Smith-Paterson. The synthesis represents current methods for controlling acyclic chemistry that utilize reactions such as allylic boronates, allenyl stannanes, oxazolidinone auxiliaries, boron enolates, and allylic silanes, as well as coupling strategies like Suzuki-Miyaura, Negishi, N
adv_org_chem_13-2-6(2)
- 1. ÓЙCºÏ³É»¯Ñ§ÌØÕ“ °k±íÙYÁÏ 2011-11-20 ÓÐÄ© ·¼ (M1) TOTAL SYNTHESIS OF DISCODERMOLIDE (pt. 2)
- 10. Lewis acid-induced addition of allylic silane to aldehyde as key-step
- 35. Discodermolide: very complex chainlike compound (13 stereocenters) Representative example of current methods for control of acyclic chemistry. - Key enantioselective reaction Allylic boronate, allenyl stannanes, oxazolidinone auxiliaries, boron enolate, and allylic silane - Key coupling strategy Suzuki-Miyaura, Negishi, NHK, and Wittig High degree of convergency, robustness, and scaled-up synthesis!!