Enantioselective synthesis of the C18-C25 segment of lasonolide A by an oxonia-cope prins cascade

被引：44

作者：

Dalgard, JE ^{[1
]}

Rychnovsky, SD ^{[1
]}

机构：

[1] Univ Calif Irvine, Dept Chem, Irvine, CA 92697 USA

来源：

ORGANIC LETTERS | 2005年 / 7卷 / 08期

关键词：

D O I：

10.1021/ol050270s

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A 2-oxonia-Cope Prins cascade was developed that led to a facile and stereoselective synthesis of the C18-C25 segment of lasonolide A. The strategy nicely handles the introduction of the quaternary center in the tetrahydropyran ring, and all of the stereogenic centers in the product arise from a single stereocenter introduced in a catalytic enantioselective reaction.

引用

收藏

页码：1589 / 1591

页数：3

相关论文

共 31 条

[1] 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

[2] Diastereoselective synthesis of 2,3,6-trisubstituted tetrahydropyran-4-ones via prins cyclizations of enecarbamates: A formal synthesis of (+)-ratjadone A [J].

Cossey, KN ;

Funk, RL .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (39) :12216-12217

[3] 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

[4] Oxonia-Cope Prins cyclizations: A facile method for the synthesis of tetrahydropyranones bearing quaternary centers [J].

Dalgard, JE ;

Rychnovsky, SD .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (48) :15662-15663

[5] 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

[6] Stereocontrolled synthesis of spirocyclopropane sugars and their application to asymmetric formation of tertiary chiral centres: A route to 2,2'-dialkylated pyranose subunit (C-18-C-23) of lasonolide A [J].

Gurjar, MK ;

Kumar, P ;

Rao, BV .

TETRAHEDRON LETTERS, 1996, 37 (47) :8617-8620

[7] Lasonolide A: Synthesis of A and B rings via a cycloetherification strategy [J].

Hart, DJ ;

Patterson, S ;

Unch, JP .

SYNLETT, 2003, (09) :1334-1338

[8] Acid-promoted prins cyclizations of enol ethers to form tetrahydropyrans [J].

Hart, DJ ;

Bennett, CE .

ORGANIC LETTERS, 2003, 5 (09) :1499-1502

[9] LASONOLIDE-A, A NEW CYTOTOXIC MACROLIDE FROM THE MARINE SPONGE FORCEPIA SP [J].

HORTON, PA ;

KOEHN, FE ;

LONGLEY, RE ;

MCCONNELL, OJ .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (13) :6015-6016

[10]

HU YQ, 1998, THESIS U CALIFORNIA

← 1 2 3 4 →