Stereocontrolled synthesis of the DE ring system of the marine alkaloid upenamide

被引：26

作者：

Kiewel, K ^{[1
]}

Luo, ZS ^{[1
]}

Sulikowski, GA ^{[1
]}

机构：

[1] Texas A&M Univ, Dept Chem, College Stn, TX 77842 USA

来源：

ORGANIC LETTERS | 2005年 / 7卷 / 23期

关键词：

D O I：

10.1021/ol051993e

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A stereocontrolled synthesis of the DE fragment (2) of the marine alkaloid upenamide (1) is described. The synthesis proceeds in 12 steps from caprolactone (10) and 20-25% overall yield.

引用

页码：5163 / 5165

页数：3

共 15 条

[1]

Andersen R. J, 1996, ALKALOIDS CHEM BIOL, V10

[2] 2-ALKOXY-3-OXOALKYL-TETRAHYDROPYRANS AND 2-ALKOXY-3-OXOALKYL-TETRAHYDROFURANS - VERSATILE INTERMEDIATES IN HETEROCYCLIC SYNTHESIS [J].

DUHAMEL, P ;

DEYINE, A ;

DUJARDIN, G ;

PLE, G ;

POIRIER, JM .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1995, (17) :2103-2114

[3] LARGE-SCALE LABORATORY ELECTROLYSIS IN ORGANIC-SYSTEMS .4. ANODIC METHOXYLATION AND ACETOXYLATION [J].

EBERSON, L ;

HLAVATY, J ;

JONSSON, L ;

NYBERG, K ;

SERVIN, R ;

STERNERUP, H ;

WISTRAND, LG .

ACTA CHEMICA SCANDINAVICA SERIES B-ORGANIC CHEMISTRY AND BIOCHEMISTRY, 1979, 33 (02) :113-115

[4] 'Upenamide:: An unprecedented macrocyclic alkaloid from the Indonesian sponge Echinochalina sp. [J].

Jiménez, JI ;

Goetz, G ;

Mau, CMS ;

Yoshida, WY ;

Scheuer, PJ ;

Williamson, RT ;

Kelly, M .

JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (25) :8465-8469

[5] Synthesis of the unusual octahydropyrano[2,3-b]pyridine ring system of ′upenamide [J].

Maia, AA ;

Mons, S ;

Gil, RPD ;

Marazano, C .

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2004, 2004 (05) :1057-1062

[6] Synthesis of substituted pyrrolidines and piperidines from endocyclic enamine derivatives.: Synthesis of (±)-laburnamine [J].

Matos, MN ;

Afonso, CAM ;

Batey, RA .

TETRAHEDRON, 2005, 61 (05) :1221-1244

[7]

Matos MRPN, 2001, TETRAHEDRON LETT, V42, P7007

[8]

MIDLAND MM, 1984, TETRAHEDRON, V40, P1371

[9]

NYBERG K, 1976, SYNTHESIS-STUTTGART, P545

[10] A stannous chloride-induced deacetalisation-cyclisation process to prepare the ABC ring system of 'upenamide [J].

Reid, M ;

Taylor, RJK .

TETRAHEDRON LETTERS, 2004, 45 (21) :4181-4183

← 1 2 →