Enantioselective Synthesis of (-)-Dysiherbaine

被引：17

作者：

Do, Ha ^{[1
]}

Kang, Chang Won ^{[1
]}

Cho, Joon Hyung ^{[1
]}

Gilbertson, Scott R. ^{[1
]}

机构：

[1] Univ Houston, Dept Chem, Houston, TX 77204 USA

来源：

ORGANIC LETTERS | 2015年 / 17卷 / 16期

关键词：

SPONGE DYSIDEA-HERBACEA; AMINO-ACID; MARINE SPONGE; KAINATE RECEPTORS; NEODYSIHERBAINE-A; LEWIS-ACIDS; DYSIHERBAINE; REARRANGEMENT; ANALOGS;

D O I：

10.1021/acs.orglett.5b01821

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Dysiherbaine, a natural product isolated from the Marine sponge Dysidea herbacea, has been shown to be a selective agonist of non-NMDA type glutamate receptors, kainate receptors. An enantioselective synthesis of dysiherbaine is reported. Metathesis of the diene followed by conversion of the resulting alkene to the amino alcohol and addition of the amino acid provides the natural product. This synthesis differs from previous approaches to the molecule in that the functionality on the tetrahydropyran ring is installed late in the route.

引用

页码：3972 / 3974

页数：3

共 50 条

[1] Total synthesis of (-)-dysiherbaine
Celindro, Nelma Carurucan
Kim, Tae Woo
Kang, Sung Ho
CHEMICAL COMMUNICATIONS, 2012, 48 (50) : 6295 - 6297
[2] A Formal Total Synthesis of Dysiherbaine and Neodysiherbaine A
Lee, Hee-Yoon
Lee, Sang-Shin
Kim, Hoon Seok
Lee, Kang Mun
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2012, 2012 (22) : 4192 - 4199
[3] Synthesis of the dysiherbaine tetrahydropyran core utilizing improved tethered aminohydroxylation conditions
Carroll, Christopher L.
Chamberlin, A. Richard
TETRAHEDRON LETTERS, 2011, 52 (31) : 3995 - 3997
[4] Total synthesis of dysiherbaine and neodysiherbaine A
Cachet, Xavier
Poree, Francois-Hugues
RSC ADVANCES, 2013, 3 (31): : 12466 - 12484
[5] A formal total synthesis of (-)-dysiherbaine
Kang, SH
Lee, YM
SYNLETT, 2003, (07) : 993 - 994
[6] Pharmacological activity of C10-substituted analogs of the high-affinity kainate receptor agonist dysiherbaine
Lash-Van Wyhe, L. Leanne
Postila, Pekka A.
Tsubone, Koichi
Sasaki, Makoto
Pentikainen, Olli T.
Sakai, Ryuichi
Swanson, Geoffrey T.
NEUROPHARMACOLOGY, 2010, 58 (03) : 640 - 649
[7] Enantioselective Synthesis of (+)-N-(Desmethyl)dysibetaine CPb
Tanaka, Kento
Sakai, Michihiro
Takamizawa, Satoshi
Oikawa, Masato
CHEMISTRY LETTERS, 2015, 44 (03) : 253 - 255
[8] Stereoselective synthesis of the (-)-dysiherbaine furopyran core via BF3-promoted formal [3+2] annulation of aldehydo-aldoses with allylsilanes
Hotoda, Koki
Ohnuma, Asami
Kusakabe, Kosuke
Tanaka, Aid
Sasaki, Ikuo
Sugimura, Hideyuki
TETRAHEDRON LETTERS, 2016, 57 (48) : 5359 - 5362
[9] Advances in the enantioselective synthesis of carbocyclic nucleosides
Boutureira, Omar
Isabel Matheu, M.
Diaz, Yolanda
Castillon, Sergio
CHEMICAL SOCIETY REVIEWS, 2013, 42 (12) : 5056 - 5072
[10] Design, synthesis, and biological evaluation of a scaffold for iGluR ligands based on the structure of (-)-dysiherbaine
Cohen, JL
Limon, A
Miledi, R
Chamberlin, AR
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2006, 16 (08) : 2189 - 2194

← 1 2 3 4 5 →