Cyclopentanes from N-amino-glyconolactams.: A synthesis of mannostatin A

被引：10

作者：

Hu, GX ^{[1
]}

Zimmermann, M ^{[1
]}

Ramana, CV ^{[1
]}

Vasella, A ^{[1
]}

机构：

[1] ETH Honggerberg, Organ Chem Lab, CH-8093 Zurich, Switzerland

来源：

CHEMICAL COMMUNICATIONS | 2003年 / 08期

关键词：

D O I：

10.1039/b301213a

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Oxidation of a N-amino-ribonolactam with lead tetraacetate yields two cyclopentanes; the major one was transformed into the alpha-mannosidase inhibitor mannostatin A.

引用

页码：952 / 953

页数：2

共 40 条

[1] MANNOSTATIN-A AND MANNOSTATIN-B - NEW INHIBITORS OF ALPHA-D-MANNOSIDASE, PRODUCED BY STREPTOVERTICILLIUM-VERTICILLUS VAR QUINTUM ME3-AG3 - TAXONOMY, PRODUCTION, ISOLATION, PHYSICOCHEMICAL PROPERTIES AND BIOLOGICAL-ACTIVITIES [J].

AOYAGI, T ;

YAMAMOTO, T ;

KOJIRI, K ;

MORISHIMA, H ;

NAGAI, M ;

HAMADA, M ;

TAKEUCHI, T ;

UMEZAWA, H .

JOURNAL OF ANTIBIOTICS, 1989, 42 (06) :883-889

[2] AZIRIDINATION BY OXIDATIVE ADDITION OF N-AMINOQUINAZOLONES TO ALKENES - EVIDENCE FOR NON-INVOLVEMENT OF N-NITRENES [J].

ATKINSON, RS ;

GRIMSHIRE, MJ ;

KELLY, BJ .

TETRAHEDRON, 1989, 45 (10) :2875-2886

[3] AZIRIDINATION OF VINYLSILANES AND VINYLSTANNANES - A NEW SYNTHESIS OF AZIRINES [J].

ATKINSON, RS ;

KELLY, BJ .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1989, (13) :836-837

[4] OXIDATION OF N-AMINOQUINAZOLONES IN THE PRESENCE OF ALKENES - EVIDENCE AGAINST INVOLVEMENT OF N-NITRENES [J].

ATKINSON, RS ;

KELLY, BJ .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1987, (18) :1362-1363

[5] Synthesis and biological activity of natural aminocyclopentitol glycosidase inhibitors: Mannostatins, trehazolin, allosamidins, and their analogues [J].

Berecibar, A ;

Grandjean, C ;

Siriwardena, A .

CHEMICAL REVIEWS, 1999, 99 (03) :779-844

[6]

BISAZ R, 1975, THESIS ETH ZURICH

[7] SYNTHESIS OF CHIRAL CARBOCYCLIC NUCLEOSIDES [J].

BORTHWICK, AD ;

BIGGADIKE, K .

TETRAHEDRON, 1992, 48 (04) :571-623

[8] Acyl hydrazines as precursors to acyl radicals [J].

Braslau, R ;

Anderson, MO ;

Rivera, F ;

Jimenez, A ;

Haddad, T ;

Axon, JR .

TETRAHEDRON, 2002, 58 (27) :5513-5523

[9] THE CONVERSION OF CARBOHYDRATE-DERIVATIVES INTO FUNCTIONALIZED CYCLOHEXANES AND CYCLOPENTANES [J].

FERRIER, RJ ;

MIDDLETON, S .

CHEMICAL REVIEWS, 1993, 93 (08) :2779-2831

[10] REACTIONS OF LEAD TETRA-ACETATE .6. FURTHER REACTIONS WITH HYDRAZONES [J].

GLADSTONE, WA ;

NORMAN, ROC .

JOURNAL OF THE CHEMICAL SOCIETY C-ORGANIC, 1966, (17) :1531-+

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