Chiral synthesis of polyketide derived natural products .52. Stereoselective total synthesis of lysocellin, the representative polyether antibiotic of the lysocellin family .2. Synthesis of C10-C23 subunit via construction of two rings (B and C) and its condensation with C1-C9 subunit to achieve the total synthesis of lysocellin

被引：6

作者：

Horita, K

Tanaka, K

Inoue, T

Yonemitsu, O

机构：

[1] Faculty of Pharmaceutical Sciences, Hokkaido University

[2] Department of Chemistry, Okayama University of Science

来源：

TETRAHEDRON | 1996年 / 52卷 / 02期

关键词：

D O I：

10.1016/0040-4020(95)00906-X

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Stereoselective total synthesis of lysocellin (1), a representative polyether antibiotic, was achieved via construction of substituted tetrahydrofuran and gamma-lactol rings and final aldol condensation

引用

页码：551 / 564

页数：14

共 16 条

[1] SYNTHETIC ROUTES TO TETRAHYDROFURAN, TETRAHYDROPYRAN, AND SPIROKETAL UNITS OF POLYETHER ANTIBIOTICS AND A SURVEY OF SPIROKETALS OF OTHER NATURAL-PRODUCTS [J].

BOIVIN, TLB .

TETRAHEDRON, 1987, 43 (15) :3309-3362

[2]

CARDILLO G, 1990, J AM CHEM SOC, V46, P321

[3] LYSOCELLIN, A NEW POLYETHER ANTIBIOTIC .1. ISOLATION, PURIFICATION, PHYSICOCHEMICAL AND BIOLOGICAL PROPERTIES [J].

EBATA, E ;

KASAHARA, H ;

SEKINE, K ;

INOUE, Y .

JOURNAL OF ANTIBIOTICS, 1975, 28 (02) :118-121

[4] SYNTHETIC STUDIES IN THE LYSOCELLIN FAMILY OF POLYETHER ANTIBIOTICS - THE TOTAL SYNTHESIS OF FERENSIMYCIN-B [J].

EVANS, DA ;

POLNIASZEK, RP ;

DEVRIES, KM ;

GUINN, DE ;

MATHRE, DJ .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (20) :7613-7630

[5]

HORITA K, 1993, CHEM PHARM BULL, V41, P2044

[6] STEREOSELECTIVE TOTAL SYNTHESIS OF POLYETHER IONOPHORE ANTIBIOTICS, ISOLASALOCID-A AND LASALOCID-A .2. THE TOTAL SYNTHESIS VIA STEREOSELECTIVE CONSTRUCTION OF THE B-RINGS BY CHELATION-CONTROLLED CYCLIZATION UNDER THERMODYNAMIC CONDITIONS [J].

HORITA, K ;

NODA, I ;

TANAKA, K ;

OIKAWA, Y ;

YONEMITSU, O .

TETRAHEDRON, 1993, 49 (27) :5997-6018

[7]

HORITA K, 1996, IN PRESS TETRAHEDRON, V52, P531

[8] STUDIES ON IONOPHOROUS ANTIBIOTICS .11. ARTIFACTS AND DEGRADATION PRODUCTS OF LYSOCELLIN [J].

KOENUMA, M ;

OTAKE, N .

JOURNAL OF ANTIBIOTICS, 1977, 30 (10) :819-828

[9]

KUSAKABE Y, 1977, J ANTIBIOT, V30, P819

[10] LATENT HOMOALLYLIC IONS IN CARBOCYCLIC RING CONSTRUCTION - ALPHA-CEDRENE [J].

LANSBURY, PT ;

HADDON, VR ;

STEWART, RC .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1974, 96 (03) :896-898

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