5-Exocyclic products, 2,3,5-trisubstituted tetrahydrofurans via prins-type cyclization

被引：42

作者：

Chavre, Satish N. ^{[1
]}

Choo, Hyunah ^{[1
]}

Cha, Joo Hwan ^{[1
]}

Pae, Ae Nim ^{[1
]}

Choi, Kyung Il ^{[1
]}

Cho, Yong Seo ^{[1
]}

机构：

[1] Korea Inst Sci & Technol, Biochem Res Ctr, Seoul 130650, South Korea

来源：

ORGANIC LETTERS | 2006年 / 8卷 / 16期

关键词：

D O I：

10.1021/ol061528x

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

5-Exocyclic products, 2,3,5-trisubstituted tetrahydrofurans, were synthesized from homopropargylic alcohols with terminally substituted alkynes and various aldehydes via Prins-type cyclization. It is of interest that the exocyclic vinyl cation generated as a result of Prins-type cyclization could be trapped as a vinyl triflate when CH2Cl2 was used as a solvent, whereas in ethereal solution the vinyl cation underwent hydrolysis to give the corresponding ketone product.

引用

页码：3617 / 3619

页数：3

共 23 条

[1] SYNTHETIC ROUTES TO TETRAHYDROFURAN, TETRAHYDROPYRAN, AND SPIROKETAL UNITS OF POLYETHER ANTIBIOTICS AND A SURVEY OF SPIROKETALS OF OTHER NATURAL-PRODUCTS [J].

BOIVIN, TLB .

TETRAHEDRON, 1987, 43 (15) :3309-3362

[2]

Cassidy JH, 1997, SYNLETT, P1411

[3] Prins cyclizations in silyl additives with suppression of epimerization: Versatile tool in the synthesis of the tetrahydropyran backbone of natural products [J].

Chan, KP ;

Loh, TP .

ORGANIC LETTERS, 2005, 7 (20) :4491-4494

[4] Indium trichloride mediated intramolecular Prins-type cyclization [J].

Cho, YS ;

Kim, HY ;

Cha, JH ;

Pae, AN ;

Koh, HY ;

Choi, JH ;

Chang, MH .

ORGANIC LETTERS, 2002, 4 (12) :2025-2028

[5] Stereoselection in the prins-pinacol synthesis of acyltetrahydrofurans [J].

Cohen, F ;

MacMillan, DWC ;

Overman, LE ;

Romero, A .

ORGANIC LETTERS, 2001, 3 (08) :1225-1228

[6] Total syntheses of aminomethyl-C-dideoxyglycopyranosides and their quinamides [J].

Gremyachinskiy, DE ;

Samoshin, VV ;

Gross, PH .

TETRAHEDRON LETTERS, 2003, 44 (35) :6587-6590

[7] ZUR KENNTNIS DER PRINSSCHEN REAKTION .3. UBER DIE REAKTION VON ALLYLCARBINOL MIT ALDEHYDEN UND KETONEN [J].

HANSCHKE, E .

CHEMISCHE BERICHTE-RECUEIL, 1955, 88 (07) :1053-1061

[8] Efficient protiodesilylation of unactivated C(sp3)-SiMe2Ph bonds using tetrabutylammonium fluoride [J].

Heitzman, CL ;

Lambert, WT ;

Mertz, E ;

Shotwell, JB ;

Tinsley, JM ;

Va, P ;

Roush, WR .

ORGANIC LETTERS, 2005, 7 (12) :2405-2408

[9] STEREOCONTROLLED PREPARATION OF TETRAHYDROFURANS BY ACID-CATALYZED REARRANGEMENT OF ALLYLIC ACETALS [J].

HOPKINS, MH ;

OVERMAN, LE .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1987, 109 (15) :4748-4749

[10] STEREOCONTROLLED PREPARATION OF TETRAHYDROFURANS FROM ACID-PROMOTED REARRANGEMENTS OF ALLYLIC ACETALS [J].

HOPKINS, MH ;

OVERMAN, LE ;

RISHTON, GM .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (14) :5354-5365

← 1 2 3 →