Total Synthesis of Vinorine

被引：5

作者：

Kang, Shiyuan ^{[1
]}

Wu, Yinxia ^{[1
]}

Hu, Min ^{[1
]}

Ma, Ying ^{[1
]}

Huang, Xiangdi ^{[1
]}

Hao, Zhen ^{[1
]}

Li, Xiujuan ^{[1
]}

Chen, Wen ^{[1
,2
]}

Zhang, Hongbin ^{[1
,2
]}

机构：

[1] Yunnan Univ, Sch Pharm, Key Lab Med Chem Nat Resource, Minist Educ, Kunming 650091, Peoples R China

[2] Yunnan Univ, Yunnan Prov Ctr Res & Dev Nat Prod, Sch Pharm, Yunnan Characteris Plant Extract Lab, Kunming 650091, Peoples R China

来源：

ORGANIC LETTERS | 2023年 / 25卷 / 19期

基金：

国家重点研发计划;

关键词：

STEREOCONTROLLED TOTAL-SYNTHESIS; SARPAGINE ALKALOIDS; INDOLE ALKALOIDS; REARRANGEMENT; SUAVEOLINE; CHEMISTRY; ESTER; WELL;

D O I：

10.1021/acs.orglett.3c01041

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The asymmetric total synthesis of vinorine, a polycyclic and cage-like alkaloid, has been realized in a flexible approach. Key features of the current synthesis include an aza-Achmatowicz rearrangement/ Mannich-type cyclization to install the highly functional 9-azabicyclo[3.3.1]nonane scaffold, a high yield Fischer indole annulation to synthesize the common intermediate for sarpagine-ajamaline type alkaloids, and an Ireland-Claisen rearrangement to construct the C15-C20 bond.

引用

页码：3466 / 3470

页数：5

共 43 条

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