Stereloselective synthesis of the tetrahydropyran core of polycarvernoside A

被引：73

作者：

Barry, CS

Bushby, N

Harding, JR

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：

ORGANIC LETTERS | 2005年 / 7卷 / 13期

关键词：

D O I：

10.1021/ol050840o

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A concise and stereoselective synthesis of the tetrasubstituted tetrahydropyran core of polycavernoside A was achieved in 55% overall yield from 3-benzyloxypropanal. A stereoselective allyl transfer reaction was used in the synthesis of enol ether 18 followed by a TFA-mediated cyclization to create the three new asymmetric centers in the tetrahydropyran with complete stereocontrol in a single-pot process.

引用

收藏

页码：2683 / 2686

页数：4

相关论文

共 44 条

[1] Stereocontrolled synthesis of 2,4,5-trisubstituted tetrahydropyrans [J].

Al-Mutairi, EH ;

Crosby, SR ;

Darzi, J ;

Harding, JR ;

Hughes, RA ;

King, CD ;

Simpson, TJ ;

Smith, RW ;

Willis, CL .

CHEMICAL COMMUNICATIONS, 2001, (09) :835-836

[2] Stereoselective synthesis of 4-hydroxy-2,3,6-trisubstituted tetrahydropyrans [J].

Barry, CSJ ;

Crosby, SR ;

Harding, JR ;

Hughes, RA ;

King, CD ;

Parker, GD ;

Willis, CL .

ORGANIC LETTERS, 2003, 5 (14) :2429-2432

[3] ENANTIOMERIC (Z)-CROTYLDIISOPINOCAMPHEYLBORANE AND (E)-CROTYLDIISOPINOCAMPHEYLBORANE - SYNTHESIS IN HIGH OPTICAL PURITY OF ALL 4 POSSIBLE STEREOISOMERS OF BETA-METHYLHOMOALLYL ALCOHOLS [J].

BROWN, HC ;

BHAT, KS .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1986, 108 (02) :293-294

[4] CHIRAL SYNTHESIS VIA ORGANOBORANES .21. ALLYLBORATION AND CROTYLBORATION OF ALPHA-CHIRAL ALDEHYDES WITH DIISOPINOCAMPHEYLBORON AS THE CHIRAL AUXILIARY [J].

BROWN, HC ;

BHAT, KS ;

RANDAD, RS .

JOURNAL OF ORGANIC CHEMISTRY, 1989, 54 (07) :1570-1576

[5] Stereocontrolled synthesis of trisubstituted tetrahydropyrans [J].

Cloninger, MJ ;

Overman, LE .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (05) :1092-1093

[6] Oxonia-cope rearrangement and side-chain exchange in the prins cyclization [J].

Crosby, SR ;

Harding, JR ;

King, CD ;

Parker, GD ;

Willis, CL .

ORGANIC LETTERS, 2002, 4 (04) :577-580

[7] A USEFUL 12-I-5 TRIACETOXYPERIODINANE (THE DESS-MARTIN PERIODINANE) FOR THE SELECTIVE OXIDATION OF PRIMARY OR SECONDARY ALCOHOLS AND A VARIETY OF RELATED 12-I-5 SPECIES [J].

DESS, DB ;

MARTIN, JC .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (19) :7277-7287

[8] The synthesis of mono- and bicyclic ethers via acid catalysed ring-opening cyclisation of tetrahydropyranyl ether derivatives [J].

Dixon, DJ ;

Ley, SV ;

Tate, EW .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 2000, (12) :1829-1836

[9] New dimeric macrolide glycosides from the marine sponge Myriastra clavosa [J].

Erickson, KL ;

Gustafson, KR ;

Pannell, LK ;

Beutler, JA ;

Boyd, MR .

JOURNAL OF NATURAL PRODUCTS, 2002, 65 (09) :1303-1306

[10] On the scope of a Prins-type cyclization of oxonium ions [J].

Fráter, G ;

Müller, U ;

Kraft, P .

HELVETICA CHIMICA ACTA, 2004, 87 (11) :2750-2763

← 1 2 3 4 5 →