Total Synthesis of Sinensilactam A

被引：31

作者：

Shao, Wenbin ^{[1
]}

Huang, Jun ^{[1
]}

Guo, Kai ^{[1
]}

Gong, Jianxian ^{[1
]}

Yang, Zhen ^{[1
,2
,3
,4
]}

机构：

[1] Peking Univ, Shenzhen Grad Sch, Key Lab Chem Genom, State Key Lab Chem Oncogen, Shenzhen 518055, Peoples R China

[2] Peking Univ, Minist Educ, Key Lab Bioorgan Chem & Mol Engn, Beijing 100871, Peoples R China

[3] Peking Univ, Coll Chem & Mol Engn, Beijing Natl Lab Mol Sci, Beijing 100871, Peoples R China

[4] Peking Univ, Peking Tsinghua Ctr Life Sci, Beijing 100871, Peoples R China

来源：

ORGANIC LETTERS | 2018年 / 20卷 / 07期

基金：

美国国家科学基金会;

关键词：

N-ACYLIMINIUM IONS; INTERMOLECULAR ADDITION-REACTIONS; FORMAL TOTAL-SYNTHESIS; POLYCYCLIC MEROTERPENOIDS; BIOSYNTHETIC-PATHWAY; DIVERGENT SYNTHESIS; A-G; DISCOVERY; ACID; METABOLITES;

D O I：

10.1021/acs.orglett.8b00380

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The total synthesis of naturally occurring (+/-)-sinensilactam A was achieved in 18 steps. The key steps of this work are a rhodium-catalyzed [3 + 2] cydoaddition for construction of the two all-carbon vicinal quaternary centers and a convergent and tandem condensation of the in situ generated N-acyliminium intermediate with aldehyde 20. This enabled implementation of a unified strategy for stereoselective formation; of the tetracyclic hemiaminal core of sinensilactam A in a later stage. The total syntheses of applanatumol F and C8-epi-applanatumol D are also achieved using this strategy.

引用

页码：1857 / 1860

页数：4

共 50 条

[31] Total synthesis of crotophorbolone
Yu, Tianzi
Sun, Ying
Tu, Canhui
Chen, Ting
Fu, Shaomin
Liu, Bo
CHEMICAL SCIENCE, 2020, 11 (27) : 7177 - 7181
[32] Total synthesis of sesterterpenoids
Chen, Yuye
Zhao, Jing
Lia, Shaoping
Xu, Jing
NATURAL PRODUCT REPORTS, 2019, 36 (02) : 263 - 288
[33] Total synthesis of aspidophytine
Marino, Joseph P.
Cao, Ganfeng
TETRAHEDRON LETTERS, 2006, 47 (44) : 7711 - 7713
[34] Total Synthesis of (+)Villosol
Ping XIE
Shu Feng CHEN
Xiao Tian LIANG(Institute of Materia Medica
Chinese Chemical Letters, 1997, (02) : 103 - 106
[35] Total synthesis of aflastatin A
Evans, David
Beiger, Jason
Kattnig, Egmont
Fuller, Peter
Young, Joseph
Burch, Jason
Glorius, Frank
Zhang, Jing
Trenkle, William
Thaisrivongs, David
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2015, 249
[36] Total Synthesis of CrocaginA
Bihelovic, Filip
Stichnoth, Desiree
Surup, Frank
Mueller, Rolf
Trauner, Dirk
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2017, 56 (42) : 12848 - 12851
[37] Total synthesis of azinomycin A
Coleman, RS
Li, J
Navarro, A
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2001, 40 (09) : 1736 - 1739
[38] Total synthesis of eleutherobin
Nicolaou, KC
vanDelft, F
Ohshima, T
Vourloumis, D
Xu, JY
Hosokawa, S
Pfefferkorn, J
Kim, S
Li, TH
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1997, 36 (22): : 2520 - 2524
[39] TOTAL SYNTHESIS OF (+/-)-PENTALENENE
ANNIS, GD
PAQUETTE, LA
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1982, 104 (16) : 4504 - 4506
[40] Total Synthesis of (+)-Macquarimicin A
1600, American Chemical Society (125):

← 1 2 3 4 5 →