A Scalable Total Synthesis of (-)-Nakadomarin A

被引：28

作者：

Boeckman, Robert K., Jr. ^{[1
]}

Wang, Hui ^{[1
]}

Rugg, Kyle W. ^{[1
]}

Genung, Nathan E. ^{[1
]}

Chen, Ke ^{[1
]}

Ryder, Todd R. ^{[1
]}

机构：

[1] Univ Rochester, Dept Chem, Rochester, NY 14627 USA

来源：

ORGANIC LETTERS | 2016年 / 18卷 / 23期

关键词：

RETRO-CLAISEN REARRANGEMENT; RING-CLOSING METATHESIS; NAKADOMARIN-A; TETRACYCLIC CORE; STEREOSELECTIVE-SYNTHESIS; ASYMMETRIC-SYNTHESIS; EFFICIENT; MANZAMINE; SPONGE; ROUTE;

D O I：

10.1021/acs.orglett.6b03137

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

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 S(N)2'/reduction/Staudinger/retro-aza-Claisen sequence on scale. After spirocyclization, the synthesis of nakadomarin is completed in only six steps.

引用

页码：6136 / 6139

页数：4

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