6-HYDROXYMETHYL-1,2,4-TRIOXANES AND DERIVATIVES - AN ALTERNATIVE 1,2,4-TRIOXANE SYNTHESIS FORM BETA-GAMMA-UNSATURATED BETA-HYDROXYHYDROPEROXIDES

被引：24

作者：

BLOODWORTH, AJ

JOHNSON, KA

机构：

来源：

TETRAHEDRON LETTERS | 1994年 / 35卷 / 43期

关键词：

D O I：

10.1016/S0040-4039(00)78422-X

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Allylic hydroperoxides CH2:C(Ph)CH(OOH)CH(2)OX (X = H, CONHPh, Ac), from regiospecific photo-oxygenation of allylic alcohols CH3C(Ph):CHCH(2)OX, form hemiperoxyacetals with aldehydes or ketones which upon cyclisation with mercury(II) trifluoroacetate then reduction with sodium borohydride diastereoselectively afford 1,2,4-trioxanes with XOCH(2) substituents at C-6.

引用

收藏

页码：8057 / 8060

页数：4

相关论文

共 11 条

[1] HYDROXY-DIRECTED REGIOSELECTIVE AND DIASTEREOSELECTIVE ENE REACTION OF SINGLET OXYGEN WITH CHIRAL ALLYLIC ALCOHOLS [J].

ADAM, W ;

NESTLER, B .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (12) :5041-5049

[2]

ADAM W, 1971, J CHEM SOC CHEM COMM, P822

[3] SYNTHESIS OF 1,2,4-TRIOXANES VIA INTRAMOLECULAR OXYMERCURIATION [J].

BLOODWORTH, AJ ;

SHAH, A .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1991, (14) :947-948

[4]

BLOODWORTH AJ, 1992, J CHEM SOC CHEM COMM, P428

[5] ARTEMISININ (QINGHAOSU) - A NEW TYPE OF ANTIMALARIAL DRUG [J].

BUTLER, AR ;

WU, YL .

CHEMICAL SOCIETY REVIEWS, 1992, 21 (02) :85-90

[6]

MCCULLOUGH KJ, 1985, J CHEM SOC CHEM COMM, P590

[7] REACTIONS OF HYDROGEN PEROXIDE .3. TUNGSTIC ACID CATALYZED HYDROXYLATION OF CYCLOHEXENE IN NONAQUEOUS MEDIA [J].

PAYNE, GB ;

SMITH, CW .

JOURNAL OF ORGANIC CHEMISTRY, 1957, 22 (12) :1682-1685

[8] EXTRAORDINARILY POTENT ANTIMALARIAL COMPOUNDS - NEW, STRUCTURALLY SIMPLE, EASILY SYNTHESIZED, TRICYCLIC 1,2,4-TRIOXANES [J].

POSNER, GH ;

OH, CH ;

GERENA, L ;

MILHOUS, WK .

JOURNAL OF MEDICINAL CHEMISTRY, 1992, 35 (13) :2459-2467

[9] SYNTHESIS OF INVIVO POTENT ANTIMALARIAL 1,2,4-TRIOXANES [J].

SINGH, C ;

MISRA, D ;

SAXENA, G ;

CHANDRA, S .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1992, 2 (05) :497-500

[10] PREPARATION OF BETA-HYDROXYHYDROPEROXIDES BY PHOTOOXYGENATION OF ALLYLIC ALCOHOLS AND THEIR ELABORATION INTO 1,2,4-TRIOXANES [J].

SINGH, C .

TETRAHEDRON LETTERS, 1990, 31 (47) :6901-6902