RuCl3 Promoted Efficient Synthesis of Z-Selective Macrocyclic Thiotetralactones via Ring-Closing Metathesis

被引：2

作者：

Muthusamy, Sengodagounder ^{[1
]}

Kumar, Muniyappankovilthottam Devaraj Senthil ^{[1
]}

机构：

[1] Bharathidasan Univ, Sch Chem, Tiruchirappalli 620024, Tamil Nadu, India

来源：

CHEMISTRYSELECT | 2016年 / 1卷 / 10期

关键词：

Grubbs' catalyst; Macrocycles; Metathesis; Z-Selectivity; Thiolactones; MEDIUM-SIZED RINGS; STEREOSELECTIVE-SYNTHESIS; OLEFIN METATHESIS; ACID; HETEROCYCLES; MACROLIDES; COMPLEXES; LACTONES; SULFONES; DESIGN;

D O I：

10.1002/slct.201600350

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Ring-closing metathesis reactions of sulfur atom containing acyclic diolefins in the presence of Grubbs' catalyst and ruthenium chloride as an additive were demonstrated to afford a range of symmetrical unsaturated macrocyclic thiotetralactones with Z-selectivity having different ring sizes, spacers and sulfur atoms. The representative structure of macrocyclic thiotetralactones was characterized using single crystal X-ray analysis. Subsequent reduction of unsaturated thiolactones furnished the corresponding saturated macrocyclic thiotetralactones.

引用

页码：2439 / 2443

页数：5

共 59 条

[1] ASYMMETRY IN THE REACTION OF L-MENTHOL WITH BETA-PHENYLGLUTARIC ANHYDRIDE, AN ANALOG OF CITRIC ACID - PREPARATION OF OPTICALLY ACTIVE PYRROLIDIDES OF BETA-PHENYLGLUTARIC ACID [J].

ALTSCHUL, R ;

BERNSTEIN, P ;

COHEN, SG .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1956, 78 (19) :5091-5095

[2] A ring-closing metathesis approach toward formal total synthesis of (+)-diplodialide A [J].

Anand, RV ;

Baktharaman, S ;

Singh, VK .

JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (08) :3356-3359

[3]

[Anonymous], 2001, BIOL CHEM ELEMENTS

[4] Microwave-enhanced synthesis of N-shifted buflavine analogues via a Suzuki-ring-closing metathesis protocol [J].

Appukkuttan, P ;

Dehaen, W ;

Van der Eycken, E .

ORGANIC LETTERS, 2005, 7 (13) :2723-2726

[5] Synthesis of sulphur-containing heterocycles by ring closing diene metathesis [J].

Armstrong, SK ;

Christie, BA .

TETRAHEDRON LETTERS, 1996, 37 (52) :9373-9376

[6] A Straightforward Synthetic Entry to Cleavamine-Type Indole Alkaloids by a Ring-Closing Metathesis-Vinyl Halide Heck Cyclization Strategy [J].

Bennasar, M. -Lluisa ;

Sole, Daniel ;

Zulaica, Ester ;

Alonso, Sandra .

ORGANIC LETTERS, 2011, 13 (08) :2042-2045

[7] A convergent ring-closing metathesis approach to carbohydrate-based macrolides with potential antibiotic activity [J].

Blom, P ;

Ruttens, B ;

Van Hoof, S ;

Hubrecht, I ;

Van der Eycken, J ;

Sas, B ;

Van hemel, J ;

Vandenkerckhove, J .

JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (24) :10109-10112

[8] Structure and photochemistry of 18-diazo-1,4,7,10,13,16-hexaoxacyclononadeca-17,19-dione and its sodium and potassium complexes. Control of the ground-state conformation of 2-diazo-1,3-dicarbonyl fragment via host-guest complexation [J].

Bogdanova, A ;

Perkovic, MW ;

Popik, VV .

JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (24) :9867-9873

[9] SYNTHETIC MACROCYCLIC DIESTER AND TETRAESTER COMPOUNDS [J].

BRADSHAW, JS ;

MAAS, GE ;

IZATT, RM ;

CHRISTENSEN, JJ .

CHEMICAL REVIEWS, 1979, 79 (01) :37-52

[10]

Cao Y., 2005, J CHEM SOC CHEM COMM, P3132

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