Expeditious and stereoselective synthesis of chiral trans-β-hydroxy-δ-lactone systems

被引：18

作者：

Miyazawa, M ^{[1
]}

Matsuoka, E ^{[1
]}

Sasaki, S ^{[1
]}

Oonuma, S ^{[1
]}

Maruyama, K ^{[1
]}

Miyashita, M ^{[1
]}

机构：

[1] Hokkaido Univ, Grad Sch Sci, Div Chem, Sapporo, Hokkaido 060, Japan

来源：

CHEMISTRY LETTERS | 1998年 / 02期

关键词：

D O I：

10.1246/cl.1998.109

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Expeditious and stereoselective synthesis of chiral trans-beta-hydroxy-delta-lactone systems starting from gamma,delta-epoxy acrylates is described which involves the regioselective ring opening of an epoxide and the intramolecular conjugate addition of a hemiacetal alkoxide anion of delta-hydroxy-alpha,beta-unsaturated esters as key steps.

引用

页码：109 / 110

页数：2

共 50 条

[21] Stereoselective Synthesis of Enantiopure Oxetanes, a Carbohydrate Mimic, an ε-Lactone, and Cyclitols from Biocatalytically Derived β-Hydroxy Esters as Chiral Precursors
Das, Debabrata
Halder, Joydev
Bhuniya, Rajib
Nanda, Samik
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2014, 2014 (24) : 5229 - 5246
[22] Stereoselective synthesis of β-hydroxy-α-amino acids β-substituted with non-aromatic heterocycles
Cremonesi, Giuseppe
Croce, Piero Dalla
Fontana, Francesco
Forni, Alessandra
La Rosa, Concetta
TETRAHEDRON-ASYMMETRY, 2007, 18 (14) : 1667 - 1675
[23] Synthesis of chiral β-hydroxy-δ-lactones using an epoxide-based methodology
Vazquez-Maldonado, Luis A.
Valentin, Elizabeth
Torres, Gerardo
Prieto, Jose A.
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2013, 245
[24] Stereoselective synthesis of flavonoids .4. Trans- and cis-dihydroflavonols
vanRensburg, H
vanHeerden, PS
Bezuidenhoudt, BCB
Ferreira, D
TETRAHEDRON, 1997, 53 (41) : 14141 - 14152
[25] Highly stereoselective synthesis of C-(alkynyl)-pseudoglycals from δ-hydroxy-α,β-unsaturated aldehydes
Yadav, J. S.
Raju, A. Krishnam
Sunitha, V.
TETRAHEDRON LETTERS, 2006, 47 (30) : 5269 - 5272
[26] Stereoselective synthesis of γ-hydroxy-α-amino acids through aldolase-transaminase recycling cascades
Guerard-Helaine, Christine
Heuson, Egon
Ndiaye, Moussa
Gourbeyre, Lea
Lemaire, Marielle
Helaine, Virgil
Charmantray, Franck
Petit, Jean-Louis
Salanoubat, Marcel
de Berardinis, Veronique
Gefflaut, Thierry
CHEMICAL COMMUNICATIONS, 2017, 53 (39) : 5465 - 5468
[27] Stereoselective synthesis of anti-β-hydroxy-α-amino acids through dynamic kinetic resolution
Makino, K
Goto, T
Hiroki, Y
Hamada, Y
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2004, 43 (07) : 882 - 884
[28] β-hydroxy-γ-lactones as chiral building blocks for the enantioselective synthesis of marine natural products
García, C
Martín, T
Martín, VS
JOURNAL OF ORGANIC CHEMISTRY, 2001, 66 (04): : 1420 - 1428
[29] Stereoselective synthesis of trans-β-substituted γ-ferrocenyl-γ-butyrolactones via ammonium ylides
Shi, L
Han, Y
Yang, ZJ
Liu, WM
Liang, YM
SYNTHESIS-STUTTGART, 2005, (17): : 2851 - 2856
[30] STEREOSELECTIVE SYNTHESIS OF "(+/-)-11-HYDROXY-TRANS-8-DODECENOIC ACID LACTONE, A NATURALLY OCCURRING MACROLIDE FROM CEPHALOSPORIUM-RECIFEI
COREY, EJ
ULRICH, P
FITZPATRICK, JM
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1976, 98 (01) : 222 - 224

← 1 2 3 4 5 →