Regiochemical control in the synthesis of tetrahydrofurans by acid-catalyzed cyclization of hydroxy selenides and hydroxy sulfides

被引：34

作者：

Gruttadauria, M

Lo Meo, P

Noto, R

机构：

[1] Dipartimento Chim Organ E Paterno, I-90128 Palermo, Italy

[2] CNR, ICTPN, Natl Inst Chem Biol Syst, I-90146 Palermo, Italy

来源：

TETRAHEDRON | 1999年 / 55卷 / 15期

关键词：

D O I：

10.1016/S0040-4020(99)00149-0

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An efficient regiochemical control in the synthesis of tetrahydrofurans was achieved by acid-catalyzed cyclization of hydroxy-selenides (10a) and (11a) which cyclize in the endo/exo mode and by hydroxy-sulfides (10c) and (11c) which cyclize in the exo mode. By cyclization of the relevant hydroxy-selenides, the C15-C20 fragment of (+)-Rolliniastatin 1 was obtained. Semiempirical calculations (PM3) were used in rationalizing experimental results. (C) 1999 Elsevier Science Ltd. All rights reserved.

引用

收藏

页码：4769 / 4782

页数：14

相关论文

共 23 条

[1] 1,3-asymmetric induction in electrophilic addition onto homoallylsilanes. An approach towards the total synthesis of (+/-)-kumausyne. [J].

Andrey, O ;

Glanzmann, C ;

Landais, Y ;

ParraRapado, L .

TETRAHEDRON, 1997, 53 (08) :2835-2854

[2]

Arista L, 1997, SYNLETT, P627

[3]

Arista L, 1998, HETEROCYCLES, V48, P1325

[4]

BANKS JM, 1994, TETRAHEDRON LETT, V35, P7259

[5] REACTIONS OF EPISULFONIUM IONS FROM THE SULFENYLATION OF ALKENES AND FROM PHENYLTHIO MIGRATION - KINETIC VS THERMODYNAMIC CONTROL [J].

BIRD, P ;

EAMES, J ;

FALLIS, AG ;

JONES, RVH ;

RODDIS, M ;

STURINO, CF ;

OSULLIVAN, S ;

WARREN, S ;

WESTWELL, MS ;

WORRALL, J .

TETRAHEDRON LETTERS, 1995, 36 (11) :1909-1912

[6] Remote allylic silyloxy groups as stereocontrol elements in intramolecular oxymercurations of gamma-hydroxyalkenes [J].

Bratt, K ;

Garavelas, A ;

Perlmutter, P ;

Westman, G .

JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (06) :2109-2117

[7] REARRANGEMENTS OF PHENYLTHIO SUBSTITUTED 1,N-DIOLS WITH TOLUENE-P-SULFONIC ACID AND WITH TOLUENE-P-SULFONYL CHLORIDE [J].

DJAKOVITCH, L ;

EAMES, J ;

JONES, RVH ;

MCINTYRE, S ;

WARREN, S .

TETRAHEDRON LETTERS, 1995, 36 (10) :1723-1726

[8] Kinetic and thermodynamic control in the stereospecific synthesis of cyclic ethers via phenylsulfanyl (PhS) migration [J].

Eames, J ;

Warren, S .

TETRAHEDRON LETTERS, 1996, 37 (20) :3525-3528

[9] Stereochemically controlled synthesis of 1,8-dioxaspiro[4.5]decanes and 1-oxa-8-thiaspiro[4.5]decanes by phenylsulfanyl migration [J].

Eames, J ;

Heras, MAD ;

Jones, RVH ;

Warren, S .

TETRAHEDRON LETTERS, 1996, 37 (26) :4581-4584

[10] Efficient alkylsulfanyl (SMe, SEt and SCH(2)Ph) and sulfanyl (SH) migration in the stereospecific synthesis of substituted tetrahydrofurans [J].

Eames, J ;

Jones, RVH ;

Warren, S .

TETRAHEDRON LETTERS, 1996, 37 (27) :4823-4826