De novo asymmetric synthesis of anamarine and its analogues

被引：39

作者：

Gao, D ^{[1
]}

O'Doherty, GA ^{[1
]}

机构：

[1] W Virginia Univ, Dept Chem, Morgantown, WV 26506 USA

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2005年 / 70卷 / 24期

关键词：

D O I：

10.1021/jo051681p

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The enantioselective synthesis of anamarine has been achieved in 21 steps. The route relies on enantio- and regioselective Sharpless dihydroxylation of dienoate ester and zinc borohydride reduction to establish the C-8-C-11 stereochemistry. A diastereoselective Leighton allylation established the desired C-5 stereochemistry. The route has also been used to prepare two diastereoisomers of anamarine in 14 steps.

引用

页码：9932 / 9939

页数：8

共 50 条

[1] De novo asymmetric syntheses of muricatacin and its analogues via dihydroxylation of dienoates
Ahmed, Md. Moinuddin
Cui, Hu
O'Doherty, George A.
JOURNAL OF ORGANIC CHEMISTRY, 2006, 71 (17): : 6686 - 6689
[2] Synthesis of gem-difluoromethylenated analogues of anamarine
Lin, Jing
Qiu, Xiao-Long
Qing, Feng-Ling
JOURNAL OF FLUORINE CHEMISTRY, 2010, 131 (06) : 684 - 690
[3] De novo asymmetric synthesis of Aspergillide
Xing, Yalan
O'Doherty, George A.
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2010, 240
[4] De Novo Asymmetric Synthesis of (+)-Monanchorin
Ma, Yuzhi
O'Doherty, George A.
ORGANIC LETTERS, 2015, 17 (21) : 5280 - 5283
[5] De novo asymmetric synthesis of (-)-nanaomycin A
Zhang, Qi
O'Doherty, George A.
TETRAHEDRON, 2018, 74 (38) : 4994 - 4999
[6] Asymmetric de novo synthesis of fluorinated D-glucitol and D-mannitol analogues
Giuffredi, Guy T.
Purser, Sophie
Sawicki, Marcin
Thompson, Amber L.
Gouverneur, Veronique
TETRAHEDRON-ASYMMETRY, 2009, 20 (6-8) : 910 - 920
[7] De Novo Synthesis of Dihydrobenzofurans and Indolines and Its Application to a Modular, Asymmetric Synthesis of Beraprost
Wang, Ze-Shu
Bennett, Steven H. H.
Kicin, Bilal
Jing, Changcheng
Pradeilles, Johan A. A.
Thai, Karen
Smith, James R. R.
Bacos, P. David
Fasano, Valerio
Saunders, Carla M. M.
Aggarwal, Varinder K. K.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2023, 145 (25) : 14124 - 14132
[8] De novo synthesis of a stable epoxypyranyl molybdenum scaffold and its use in asymmetric synthesis
Garnier, Ethel
Liebeskind, Lanny S.
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2006, 231
[9] De Novo Asymmetric Synthesis of Phoracantholide J
Avocetien, Kenneth F.
Li, Jiazhen J.
Liu, Xiaofan
Wang, Yanping
Xing, Yalan
O'Doherty, George A.
ORGANIC LETTERS, 2016, 18 (19) : 4970 - 4973
[10] De Novo Asymmetric Synthesis of Fridamycin E
Chen, Qian
Mulzer, Michael
Shi, Pei
Beuning, Penny J.
Coates, Geoffrey W.
O'Doherty, George A.
ORGANIC LETTERS, 2011, 13 (24) : 6592 - 6595

← 1 2 3 4 5 →