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

1. 有機合成化学特論 発表資料
2011-11-20 有末 芳 (M1)
TOTAL SYNTHESIS OF
DISCODERMOLIDE
(pt. 2)

2. Novel
aldol-based approach

10. Lewis acid-induced
addition of allylic silane
to aldehyde as key-step

25. Hybrid of
Novartis-Smith-Paterson

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!!