UTILIZATION OF L-QUEBRACHITOL IN NATURAL PRODUCT SYNTHESIS - TOTAL SYNTHESIS AND ABSOLUTE-CONFIGURATION OF (-)-OUDEMANSIN-X

被引：16

作者：

CHIDA, N

YAMADA, K

OGAWA, S

机构：

[1] Department of Applied Chemistry, Faculty of Science and Technology, Keio University, Kohoku-ku, Yokohama 223

来源：

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 1993年 / 17期

关键词：

D O I：

10.1039/p19930001957

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The stereoselective conversion of the naturally occurring optically active cyclitol, L-quebrachitol 2, into antifungal beta-methoxyacrylate, oudemansin X 1 is described. This first total synthesis of 1 fully confirmed the proposed absolute configuration of the antibiotic and showed the importance of 2 as a versatile chiral starting material in natural product syntheses.

引用

页码：1957 / 1962

页数：6

共 37 条

[1] Ager D. J., 1990, ORG REACTIONS, V38, P1, DOI DOI 10.1002/0471264180.0R038.01
[2] DETERMINATION OF ABSOLUTE STRUCTURE OF (-)-OUDEMANSIN-B
AKITA, H
MATSUKURA, H
OISHI, T
[J]. TETRAHEDRON LETTERS, 1986, 27 (44) : 5397 - 5400
[3] AKITA H, 1984, CHEM PHARM BULL, V32, P1242
[4] THE ABSOLUTE-CONFIGURATION OF OUDEMANSIN TOTAL SYNTHESIS OF (-)-OUDEMANSIN
AKITA, H
KOSHIJI, H
FURUICHI, A
HORIKOSHI, K
OISHI, T
[J]. TETRAHEDRON LETTERS, 1983, 24 (19) : 2009 - 2010
[5] CHIRAL SYNTHESIS OF D-MYO-INOSITOL 1-PHOSPHATE STARTING FROM L-QUEBRACHITOL
AKIYAMA, T
TAKECHI, N
OZAKI, S
[J]. TETRAHEDRON LETTERS, 1990, 31 (10) : 1433 - 1434
[6] DIASTEREOSELECTIVE REDUCTION OF ALPHA-KETO ESTERS BEARING CHIRO-INOSITOL DERIVATIVES AS CHIRAL AUXILIARIES
AKIYAMA, T
NISHIMOTO, H
OZAKI, S
[J]. TETRAHEDRON LETTERS, 1991, 32 (10) : 1335 - 1338
[7] AKIYAMA T, 1991, SYNLETT, P831
[8] THE PREPARATION OF OPTICALLY-ACTIVE DELTA-2-ISOXAZOLINES VIA ADDITION OF NITRILE OXIDES TO CHIRAL ACRYLOYL ESTERS BEARING CYCLITOLS AS AUXILIARIES
AKIYAMA, T
OKADA, K
OZAKI, S
[J]. TETRAHEDRON LETTERS, 1992, 33 (39) : 5763 - 5766
[9] A CONCISE SYNTHESIS OF (-)-CONDURITOL-F FROM L-QUEBRACHITOL VIA ALCL3-NORMAL-BU4NI MEDIATED DEMETHYLATION
AKIYAMA, T
SHIMA, H
OZAKI, S
[J]. TETRAHEDRON LETTERS, 1991, 32 (40) : 5593 - 5596
[10] ANGYAL SJ, 1963, METHODS CARBOHYDR CH, V2, P87

← 1 2 3 4 →