Regioselective Dieckmann cyclisations leading to enantiopure highly functionalised tetramic acid derivatives

被引：72

作者：

Andrews, MD

Brewster, AG

Crapnell, KM

Ibbett, AJ

Jones, T

Moloney, MG

Prout, K

Watkin, D

机构：

[1] Univ Oxford, Dyson Perrins Lab, Dept Chem, Oxford OX1 3QY, England

[2] Univ Oxford, Chem Crystallog Lab, Oxford OX1 3PD, England

[3] Zeneca Pharmaceut, Macclesfield SK10 4TG, Cheshire, England

来源：

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 1998年 / 02期

关键词：

D O I：

10.1039/a706014i

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Regioselective Dieckmann cyclisations using an N-acyloxazolidine derived from L-serine give substituted tetramic adds in high yield and enantioselectivity, The products are easily deprotected under mild conditions to give hydroxymethyltetramic acids.

引用

页码：223 / 235

页数：13

共 59 条

[51] APPROACHES TO THE SYNTHESIS OF CYTOCHALASANS .2. PYRROLINONE DERIVATIVES AS BASIC UNITS
SCHMIDLIN, T
TAMM, C
[J]. HELVETICA CHIMICA ACTA, 1980, 63 (01) : 121 - 131
[52] ALPHA-ALKYLATION OF SERINE WITH SELF-REPRODUCTION OF THE CENTER OF CHIRALITY
SEEBACH, D
AEBI, JD
[J]. TETRAHEDRON LETTERS, 1984, 25 (24) : 2545 - 2548
[53] STEREOSELECTIVE ALKYLATION AT C(ALPHA) OF SERINE, GLYCERIC ACID, THREONINE, AND TARTARIC ACID INVOLVING HETEROCYCLIC ENOLATES WITH EXOCYCLIC DOUBLE-BONDS
SEEBACH, D
AEBI, JD
GANDERCOQUOZ, M
NAEF, R
[J]. HELVETICA CHIMICA ACTA, 1987, 70 (04) : 1194 - 1216
[54] Self-regeneration of stereocenters (SRS) - Applications, limitations, and abandonment of a synthetic principle
Seebach, D
Sting, AR
Hoffmann, M
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1996, 35 (23-24): : 2708 - 2748
[55] STRUCTURE AND REACTIVITY OF 5-RING AND 6-RING N,N-ACETALS, N,O-ACETALS, AND O,O-ACETALS - A LESSON IN ALLYLIC 1,3-STRAIN (A(1,3) STRAIN)
SEEBACH, D
LAMATSCH, B
AMSTUTZ, R
BECK, AK
DOBLER, M
EGLI, M
FITZI, R
GAUTSCHI, M
HERRADON, B
HIDBER, PC
IRWIN, JJ
LOCHER, R
MAESTRO, M
MAETZKE, T
MOURINO, A
PFAMMATTER, E
PLATTNER, DA
SCHICKLI, C
SCHWEIZER, WB
SEILER, P
STUCKY, G
PETTER, W
ESCALANTE, J
JUARISTI, E
QUINTANA, D
MIRAVITLLES, C
MOLINS, E
[J]. HELVETICA CHIMICA ACTA, 1992, 75 (03) : 913 - 934
[56] Seebach D, 1986, MODERN SYNTHETIC MET, V4, P125
[57] SHELDRICK GM, 1985, J CHEM SOC P1
[58] CHEMOSELECTIVE DIECKMANN-LIKE CONDENSATIONS USING N-METHOXY-N-METHYLAMIDES
SIBI, MP
CHRISTENSEN, JW
KIM, SG
EGGEN, M
STESSMAN, C
OIEN, L
[J]. TETRAHEDRON LETTERS, 1995, 36 (35) : 6209 - 6212
[59] Taylor E. C., 1988, ORG SYNTH COLL, VVI, P549

← 1 2 3 4 5 6 →