Total synthesis of the alkaloid (-)-codonopsinine from L-xylose

被引：36

作者：

Chandrasekhar, S ^{[1
]}

Jagadeshwar, V ^{[1
]}

Prakash, SJ ^{[1
]}

机构：

[1] Indian Inst Chem Technol, Hyderabad 500007, Andhra Pradesh, India

来源：

TETRAHEDRON LETTERS | 2005年 / 46卷 / 17期

关键词：

Julia olefination; intramolecular cyclisation;

D O I：

10.1016/j.tetlet.2005.02.140

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The enantiopure total synthesis of (-)-codonopsinine is described from commercially available L-xylose in 20% overall yield. The key steps included Julia trans olefination and cascade epoxidation cyclisation strategies. (c) 2005 Elsevier Ltd. All rights reserved.

引用

页码：3127 / 3129

页数：3

共 18 条

[1] Synthesis of a val-pro diaminodiol dipeptide isostere by epoxyamine cyclization
Benedetti, F
Berti, F
Dinon, F
Nardin, G
Norbedo, S
[J]. ORGANIC LETTERS, 2004, 6 (06) : 1017 - 1019
[2] Blakemore PR, 1998, SYNLETT, P26
[3] Iterative organometallic addition to chiral hydroxylated cyclic nitrones:: Highly stereoselective syntheses of α,α′- and α,α-substituted hydroxypyrrolidines
Goti, A
Cicchi, S
Mannucci, V
Cardona, F
Guarna, F
Merino, P
Tejero, T
[J]. ORGANIC LETTERS, 2003, 5 (22) : 4235 - 4238
[4] Haddad M, 2003, SYNLETT, P274
[5] STEREOCHEMICAL REVISION AND ABSOLUTE-CONFIGURATION OF CODONOPSININE
IIDA, H
YAMAZAKI, N
KIBAYASHI, C
NAGASE, H
[J]. TETRAHEDRON LETTERS, 1986, 27 (44) : 5393 - 5396
[6] JOSEPH R, 1987, CARBOHYD RES, V163, P169
[7] MATKHALIKOVA S F, 1969, KHIM PRIR SOEDIN (TASHK), V5, P30
[8] Matkhalikova S. F., 1969, KHIM PRIR SOEDIN+, V5, P607
[9] Matkhalikova S F, 1969, KHIM PRIR SOEDIN+, V5, P606
[10] MATKHALIKOVA SF, 1971, FARMAKOL ALKALOIDOV, P210

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