Stereocontrolled synthesis of 2,4,5-trisubstituted tetrahydropyrans

被引：71
作者：
Al-Mutairi, EH
Crosby, SR
Darzi, J
Harding, JR
Hughes, RA
King, CD
Simpson, TJ
Smith, RW
Willis, CL
机构：
[1] Univ Bristol, Sch Chem, Bristol BS8 1TS, Avon, England
[2] AstraZeneca UK Ltd, Macclesfield SK10 4TG, Cheshire, England
来源：
CHEMICAL COMMUNICATIONS | 2001年 / 09期
关键词：
D O I：
10.1039/b101414p
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
Cyclisation of homoallylic acetals under acidic conditions leads to the formation of 2,4,5-trisubstituted tetrahydropyrans with the creation of two new asymmetric centres with excellent stereocontrol. By varying the acid and the nucleophile, the reaction may be adapted for the preparation of 2,4,5-trisubstituted tetrahydropyrans with either a halide, alcohol, acetate or amide at C-4.
引用
收藏
页码：835 / 836
页数：2
相关论文
共 21 条
[11]   Synthesis of the C22-C26 tetrahydropyran segment of phorboxazole by a stereoselective Prins cyclization [J].
Rychnovsky, SD ;
Thomas, CR .
ORGANIC LETTERS, 2000, 2 (09) :1217-1219
[12]   Prins desymmetrization of a C-2-symmetric diol: Application to the synthesis of 17-deoxyroflamycoin [J].
Rychnovsky, SD ;
Yang, G ;
Hu, YQ ;
Khire, UR .
JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (10) :3022-3023
[13]   Segment-coupling prins cyclizations [J].
Rychnovsky, SD ;
Hu, YQ ;
Ellsworth, B .
TETRAHEDRON LETTERS, 1998, 39 (40) :7271-7274
[14]  
Snider B. B., COMPREHENSIVE ORGANI, V2, P527, DOI DOI 10.1016/B978-0-08-052349-1.00040-8
[15]   REACTION OF ALPHA OLEFINS WITH PARAFORMALDEHYDE AND HYDROGEN HALIDES . A NOVEL TETRAHYDROPYRAN SYNTHESIS [J].
STAPP, PR .
JOURNAL OF ORGANIC CHEMISTRY, 1969, 34 (03) :479-&
[16]  
VISMANATHAN GS, 1999, ORG LETT, V1, P993
[17]   LEWIS ACID PROMOTED CONDENSATION OF CARBONYL-COMPOUNDS WITH ALKOXY-ALLYLSILANES - SYNTHESIS OF SUBSTITUTED TETRAHYDROPYRANS [J].
WEI, ZY ;
LI, JS ;
WANG, D ;
CHAN, TH .
TETRAHEDRON LETTERS, 1987, 28 (30) :3441-3444
[18]   A SELECTIVE SYNTHESIS OF 3-ALKYL-4-HALOTETRAHYDROPYRANS VIA THE TITANIUM TETRAHALIDE PROMOTED CYCLIZATION OF UNSATURATED ACETALS [J].
WINSTEAD, RC ;
SIMPSON, TH ;
LOCK, GA ;
SCHIAVELLI, MD ;
THOMPSON, DW .
JOURNAL OF ORGANIC CHEMISTRY, 1986, 51 (02) :275-277
[19]   Highly effective synthesis of 4-halo-tetrahydropyrans via a highly diastereoselective in situ prins-type cyclization reaction [J].
Yang, J ;
Viswanathan, GS ;
Li, CJ .
TETRAHEDRON LETTERS, 1999, 40 (09) :1627-1630
[20]   Diastereoselective synthesis of 2,4-disubstituted tetrahydropyranols and ethers via a Prins-type cyclization catalyzed by scandium triflate [J].
Zhang, WC ;
Li, CJ .
TETRAHEDRON, 2000, 56 (16) :2403-2411
123