A general procedure to enantiopure conduritols:: Sulfur-mediated synthesis of (+)-conduritol B and (-)-conduritol F derivatives and of (-)-conduritol E and F

被引：35

作者：

Cerè, V ^{[1
]}

Mantovani, G ^{[1
]}

Peri, F ^{[1
]}

Pollicino, S ^{[1
]}

Ricci, A ^{[1
]}

机构：

[1] Univ Bologna, Dept Organ Chem, I-40136 Bologna, Italy

来源：

TETRAHEDRON | 2000年 / 56卷 / 09期

关键词：

biologically active compounds; cyclitols; enantiomeric purity; thiosugars;

D O I：

10.1016/S0040-4020(00)00011-9

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

We have demonstrated the generality of a simple procedure, synthesizing enatiomerically pare (+)-conduritol B and (-)-conduritol F derivatives, starting, starting from D-mannitol and D-sorbitol, respectively. This method, slightly modified, can also be applied to the synthesis of unprotected conduritols: (-)-conduritol E and (-)-conduritol F were obtained. (C) 2000 Elsevier Science Ltd. All rights reserved.

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页码：1225 / 1231

页数：7

相关论文

共 24 条

[1] BIOLOGICAL-ACTIVITIES OF CYCLOPHELLITOL [J].

ATSUMI, S ;

IINUMA, H ;

NOSAKA, C ;

UMEZAWA, K .

JOURNAL OF ANTIBIOTICS, 1990, 43 (12) :1579-1585

[2] Synthesis of conduritols and related compounds [J].

Balci, M .

PURE AND APPLIED CHEMISTRY, 1997, 69 (01) :97-104

[3] CONDURITOLS AND RELATED-COMPOUNDS [J].

BALCI, M ;

SUTBEYAZ, Y ;

SECEN, H .

TETRAHEDRON, 1990, 46 (11) :3715-3742

[4] COMPLEMENTARY ENANTIOSPECIFIC SYNTHESES OF CONDURITOL-E EPOXIDES FROM HALOBENZENES [J].

CARLESS, HAJ .

TETRAHEDRON LETTERS, 1992, 33 (42) :6379-6382

[5] Protecting group-directed, diastereoselective samarium diiodide-promoted carbocyclization: Application to the synthesis of cyclitols [J].

Carpintero, M ;

FernandezMayoralas, A ;

Jaramillo, C .

JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (07) :1916-1917

[6] A NEW ONE-FLASK RAMBERG-BACKLUND REACTION [J].

CHAN, TL ;

FONG, S ;

LI, Y ;

MAN, TO ;

POON, CD .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1994, (15) :1771-1772

[7] A STEREOSELECTIVE ROUTE TO ENANTIOMERICALLY PURE MYOINOSITOL DERIVATIVES STARTING FROM D-MANNITOL [J].

CHIARA, JL ;

MARTINLOMAS, M .

TETRAHEDRON LETTERS, 1994, 35 (18) :2969-2972

[8]

CLOUGH JM, 1991, COMPREHENSIVE ORGANI, V3, P861

[9] THIOSUGARS FROM D-MANNITOL [J].

FUZIER, M ;

LEMERRER, Y ;

DEPEZAY, JC .

TETRAHEDRON LETTERS, 1995, 36 (36) :6443-6446

[10] BACTERIAL METABOLISM OF PARA-XYLENE AND META-XYLENE - OXIDATION OF AROMATIC RING [J].

GIBSON, DT ;

MAHADEVAN, V ;

DAVEY, JF .

JOURNAL OF BACTERIOLOGY, 1974, 119 (03) :930-936