Enantioselective synthesis of the larger fragment of pamamycin-607

被引：28

作者：

Bernsmann, H ^{[1
]}

Gruner, M ^{[1
]}

Metz, P ^{[1
]}

机构：

[1] Tech Univ Dresden, Inst Organ Chem, D-01062 Dresden, Germany

来源：

TETRAHEDRON LETTERS | 2000年 / 41卷 / 40期

关键词：

antibiotics; sultones; desulfurization; Mitsunobu reaction;

D O I：

10.1016/S0040-4039(00)01308-3

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The enantiomerically pure methyl ester of the complete larger hydroxy acid (C(1)-C(18)) of the macrodiolide antibiotic pamamycin-607 has been synthesized using a general sultone route to actic acids and analogs. The requisite N,N-dimethylamino moiety was introduced by Mitsunobu inversion with hydrazoic acid followed by a reaction cascade involving hydrogenation and double reductive methylation. (C) 2000 Elsevier Science Ltd. All rights reserved.

引用

页码：7629 / 7633

页数：5

共 31 条

[1]

Arista L, 1997, SYNLETT, P627

[2] Toward the synthesis of pamamycin-607 [J].

Bernsmann, H ;

Hungerhoff, B ;

Fechner, R ;

Fröhlich, R ;

Metz, P .

TETRAHEDRON LETTERS, 2000, 41 (11) :1721-1724

[3] Catalytic, asymmetric synthesis of the C1′-C10′ segment of pamamycin 621A [J].

Calter, MA ;

Bi, FC .

ORGANIC LETTERS, 2000, 2 (11) :1529-1531

[4] A GENERAL ENANTIOSELECTIVE SYNTHESIS OF ALPHA-ARYLETHYLAMINES [J].

CHEN, CP ;

PRASAD, K ;

REPIC, O .

TETRAHEDRON LETTERS, 1991, 32 (49) :7175-7178

[5]

GRAFE U, 1994, PHARMAZIE, V49, P343

[6]

Greene T. W., 1999, PROTECTIVE GROUPS OR

[7] Protonophoric activities of helioferin and pamamycin, lipophilic tertiary amine antibiotics from Mycogone rosea and Streptomyces aurantiacus [J].

Grigoriev, P ;

Berg, A ;

Schlegel, R ;

Grafe, U .

BIOELECTROCHEMISTRY AND BIOENERGETICS, 1996, 39 (02) :295-298

[8]

Härtl A, 1998, J ANTIBIOT, V51, P1040

[9] ISOLATION, PHYSICOCHEMICAL PROPERTIES AND BIOLOGICAL-ACTIVITY OF PAMAMYCIN-607, AN AERIAL MYCELIUM-INDUCING SUBSTANCE FROM STREPTOMYCES-ALBONIGER [J].

KONDO, S ;

YASUI, K ;

NATSUME, M ;

KATAYAMA, M ;

MARUMO, S .

JOURNAL OF ANTIBIOTICS, 1988, 41 (09) :1196-1204

[10] STRUCTURE OF PAMAMYCIN-607, AN AERIAL MYCELIUM-INDUCING SUBSTANCE OF STREPTOMYCES-ALBONIGER [J].

KONDO, S ;

YASUI, K ;

KATAYAMA, M ;

MARUMO, S ;

KONDO, T ;

HATTORI, H .

TETRAHEDRON LETTERS, 1987, 28 (47) :5861-5864

← 1 2 3 4 →