A Scalable Total Synthesis of (−)-Nakadomarin A
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- 作者：Robert K. Boeckman Jr. ; Hui Wang ; Kyle W. Rugg ; Nathan E. Genung ; Ke Chen ; Todd R. Ryder
- 刊名：Organic Letters
- 出版年：2016
- 出版时间：December 2, 2016
- 年：2016
- 卷：18
- 期：23
- 页码：6136-6139
- 全文大小：406K
- ISSN：1523-7052
文摘
The convergent total synthesis of the manzamine alkaloid (−)-nakadomarin A (1) is described. The retrosynthetic analysis recognized spirocycle 3, assembled via an organocatalyst-promoted Michael addition/cyclization between bicyclic lactam 4 and furan aldehyde 5, both accessible from achiral starting materials and on a multigram scale. Lactam 4 is assembled through an SN2′/reduction/Staudinger/retro-aza-Claisen sequence on scale. After spirocyclization, the synthesis of nakadomarin is completed in only six steps.