Enantiopure piperidines via stereoselective Ireland-Claisen rearrangement: entry into corynanthe alkaloids

被引：0

作者：

Udris, Niklavs ^{[1
,3
]}

Locmele, Rebeka ^{[1
,3
]}

Pelss, Juris ^{[1
]}

Ture, Anastasija ^{[1
]}

Sakaine, Guna ^{[1
]}

Kinens, Artis ^{[1
,2
]}

Smits, Gints ^{[1
,3
]}

机构：

[1] Latvian Inst Organ Synth, Aizkraukles 21, LV-1006 Riga, Latvia

[2] Univ Latvia, Fac Med & Life Sci, Jelgavas 1, LV-1004 Riga, Latvia

[3] Riga Tech Univ, Fac Nat Sci & Technol, Paula Valdena 3, LV-1048 Riga, Latvia

来源：

ORGANIC CHEMISTRY FRONTIERS | 2025年 / 12卷 / 06期

关键词：

MITRAGYNINE; QUINOLIZIDINES; STRATEGY; CINCHONA;

D O I：

10.1039/d4qo02235a

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A fully stereo-divergent Ireland-Claisen rearrangement of achiral lactones has been developed, enabling access to all four possible stereoisomers of 3,4-disubstituted piperidines and pyrrolidines. The utility of these building blocks has been showcased in the total synthesis of meroquinene ester and cardioprotective indole alkaloids sitsirikine and dihydrositsirikine.

引用

页码：1945 / 1950

页数：6

共 50 条

[1] Stereoselective Synthesis of Quaternary Carbons via the Dianionic Ireland-Claisen Rearrangement
Crimmins, Michael T.
Knight, John D.
Williams, Philip S.
Zhang, Yan
ORGANIC LETTERS, 2014, 16 (09) : 2458 - 2461
[2] Synthesis of Tubuphenylalanines via Ireland-Claisen Rearrangement
Becker, Dominic
Kazmaier, Uli
JOURNAL OF ORGANIC CHEMISTRY, 2013, 78 (01): : 59 - 65
[3] Stereoselective Synthesis of α-Fluoro Carboxylic Acids by Ireland-Claisen Rearrangement
Paola, Elena L.
Borum, Alana
Podunavac, Masa
Zakarian, Armen
ORGANIC LETTERS, 2023, : 6167 - 6171
[4] Chirality transfer in an Ireland-Claisen rearrangement:: a new approach toward the Iboga alkaloids
Höck, S
Koch, F
Borschberg, HJ
TETRAHEDRON-ASYMMETRY, 2004, 15 (11) : 1801 - 1808
[5] ORIGIN OF THE RATE ACCELERATION IN THE IRELAND-CLAISEN REARRANGEMENT
GAJEWSKI, JJ
EMRANI, J
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1984, 106 (19) : 5733 - 5734
[6] DIASTEREOSELECTIVE IRELAND-CLAISEN REARRANGEMENT OF ALLYLIC ALCOHOLS
CHA, JK
LEWIS, SC
TETRAHEDRON LETTERS, 1984, 25 (46) : 5263 - 5266
[7] The Exocyclic Olefin Geometry Control via Ireland-Claisen Rearrangement: Stereoselective Total Syntheses of Barmumycin and Limazepine E
Smits, Gints
Zemribo, Ronalds
ORGANIC LETTERS, 2013, 15 (17) : 4406 - 4409
[8] Stereodivergence in the Ireland-Claisen Rearrangement of α-Alkoxy Esters
Podunavac, Masa
Lacharity, Jacob J.
Jones, Kerry E.
Zakarian, Armen
ORGANIC LETTERS, 2018, 20 (16) : 4867 - 4870
[9] Angelic acid esters in the Ireland-Claisen rearrangement
Frost, Sarah
Campbell, Martin J.
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2007, 233 : 797 - 797
[10] Attempts To Improve the Overall Stereoselectivity of the Ireland-Claisen Rearrangement
Chen, Chi-Li
Namba, Kosuke
Kishi, Yoshito
ORGANIC LETTERS, 2009, 11 (02) : 409 - 412

← 1 2 3 4 5 →