MODEL STUDIES DIRECTED TOWARDS MICROALGAL POLYETHER TOXINS - USE OF 2-PHENYL-SULFONYL CYCLIC ETHERS IN THE PREPARATION OF TRANS, SYN, TRANS ALPHA-ALKYL, BETA-HYDROXY-SUBSTITUTED TETRAHYDROPYRAN SUBUNITS

被引：26

作者：

ALVAREZ, E ^{[1
]}

RICO, M ^{[1
]}

RODRIGUEZ, RM ^{[1
]}

ZURITA, D ^{[1
]}

MARTIN, JD ^{[1
]}

机构：

[1] UNIV LA LAGUNA,CSIC,CTR PROD NAT ORGAN ANTONIO GONZALEZ,CTRA LA ESPERANZA 2,E-38206 LA LAGUNA,SPAIN

来源：

TETRAHEDRON LETTERS | 1992年 / 33卷 / 23期

关键词：

2-PHENYLSULFONYL CYCLIC ETHERS; TRANS-FUSED POLYETHER TOXINS;

D O I：

10.1016/S0040-4039(00)92095-1

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A synthesis of opticaLLy active C-7- and C-8 -tetrahydropyranyl subunits with suitable functionalities for further elaboration of transfused polyether toxins was achieved from glucal acetate via the use of 2-phenylsulphonyl intermediates. The bicyclic trans,syn,trans oxane-oxepanyl substructure 26 was prepared through the application of this methodology.

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页码：3385 / 3388

页数：4

相关论文

共 16 条

[1] MODEL STUDIES DIRECTED TOWARDS MICROALGA POLYETHER TOXINS - A STEREOSELECTIVE ENTRY INTO C8 OXEPANE SUBUNITS [J].

ALVAREZ, E ;

DIAZ, MT ;

PEREZ, R ;

MARTIN, JD .

TETRAHEDRON LETTERS, 1991, 32 (20) :2241-2244

[2] MODEL STUDIES DIRECTED TOWARDS MICROALGA POLYETHER TOXINS - A STEREOSELECTIVE ENTRY INTO C10 CIS-FUSED AND TRANS-FUSED OXANE-OXEPANE SUBUNITS [J].

ALVAREZ, E ;

ZURITA, D ;

MARTIN, JD .

TETRAHEDRON LETTERS, 1991, 32 (20) :2245-2248

[3] D-GLYCOPYRANOSYL PHENYLSULFONES - ACYLATION OF THEIR LITHIATED ANIONS AND REDUCTIVE DESULFONYLATION OF THE RESULTING ACYLATED SULFONES - A SYNTHESIS OF ALPHA-D-C-GLYCOSIDES [J].

BEAU, JM ;

SINAY, P .

TETRAHEDRON LETTERS, 1985, 26 (50) :6193-6196

[4] D-GLYCOPYRANOSYL PHENYLSULFONES - THEIR USE IN A STEREOCONTROL SYNTHESIS OF CIS-2,6-DISUBSTITUTED TETRAHYDROPYRANS (BETA-D-C-GLYCOSIDES) [J].

BEAU, JM ;

SINAY, P .

TETRAHEDRON LETTERS, 1985, 26 (50) :6189-6192

[5] PREPARATION AND REDUCTIVE LITHIATION OF 2-DEOXY-D-GLUCOPYRANOSYL PHENYLSULFONES - A HIGHLY STEREOSELECTIVE ROUTE TO C-GLYCOSIDES [J].

BEAU, JM ;

SINAY, P .

TETRAHEDRON LETTERS, 1985, 26 (50) :6185-6188

[6] SUBSTITUTION-REACTIONS OF 2-BENZENESULFONYL CYCLIC ETHERS WITH CARBON NUCLEOPHILES [J].

BROWN, DS ;

BRUNO, M ;

DAVENPORT, RJ ;

LEY, SV .

TETRAHEDRON, 1989, 45 (13) :4293-4308

[7] DIRECT SUBSTITUTION OF 2-BENZENESULFONYL CYCLIC ETHERS USING ORGANOZINC REAGENTS [J].

BROWN, DS ;

LEY, SV .

TETRAHEDRON LETTERS, 1988, 29 (38) :4869-4872

[8] USE OF 2-PHENYLSULFONYL CYCLIC ETHERS IN THE PREPARATION OF TETRAHYDROPYRAN AND TETRAHYDROFURAN ACETALS AND IN SOME GLYCOSIDATION REACTIONS [J].

BROWN, DS ;

LEY, SV ;

VILE, S ;

THOMPSON, M .

TETRAHEDRON, 1991, 47 (07) :1329-1342

[9] SYNTHESIS OF 2-DEOXY-BETA-C-PYRANOSIDES BY DIASTEREOSELECTIVE HYDROGEN-ATOM TRANSFER [J].

CRICH, D ;

LIM, LBL .

TETRAHEDRON LETTERS, 1990, 31 (13) :1897-1900

[10] A CONCISE SYNTHESIS OF 3-DEOXY-2-O-METHYL-4,5,7-TRI-O-BENZYL-D-ARABINO-HEPTULOSONIC ACID AND RELATED-COMPOUNDS FROM 3,4,6-TRI-O-BENZYL-D-GLUCAL [J].

CRICH, D ;

RITCHIE, TJ .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1988, (15) :985-986