Synthesis of enamides from aldehydes and amides

被引：68

作者：

Bayer, A ^{[1
]}

Maier, ME ^{[1
]}

机构：

[1] Univ Tubingen, Inst Organ Chem, D-72076 Tubingen, Germany

来源：

TETRAHEDRON | 2004年 / 60卷 / 31期

关键词：

enamides; cross-coupling; N; S-acetals; benzolactones;

D O I：

10.1016/j.tet.2004.05.082

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A range of double unsaturated amides (15, 19, and 21), obtained by cross-coupling reactions was reacted with aldehydes to hemiaminals. Heating the hemiaminals in the presence of Ac2O and pyridine affected clean conversion to the corresponding enamides, such as 42, 45, and 47. Alternatively, N,S-acetals were prepared which were oxidized to the sulfones. Treatment with base also gave the enamides, favoring the cis-isomer. However, this method is less general. Application of these methods led to the natural products lansiumamide-A (30_cis), lansiumamide-I (31) and lansiumamide-B (32). (C) 2004 Elsevier Ltd. All rights reserved.

引用

页码：6665 / 6677

页数：13

共 39 条

[1] Novel marine and microbial natural product inhibitors of vacuolar ATPase [J].

Beutler, JA ;

McKee, TC .

CURRENT MEDICINAL CHEMISTRY, 2003, 10 (09) :787-796

[2]

Boyd MR, 2001, J PHARMACOL EXP THER, V297, P114

[3]

BRANDSMA L, 1990, SYNTHESIS-STUTTGART, P984

[4] Addition of acrylamide to amino aldehydes to generate non-Baylis-Hillman adducts.: Formation of novel N-acylhemiaminals [J].

Bussolari, JC ;

Beers, K ;

Lalan, P ;

Murray, WV ;

Gauthier, D ;

McDonnell, P .

CHEMISTRY LETTERS, 1998, (08) :787-788

[5] Total synthesis of (+)-crocacin D [J].

Chakraborty, TK ;

Laxman, P .

TETRAHEDRON LETTERS, 2002, 43 (14) :2645-2648

[6] A new indole derivative from the red alga Chondria atropurpurea.: Isolation, structure determination, and anthelmintic activity [J].

Davyt, D ;

Entz, W ;

Fernandez, R ;

Mariezcurrena, R ;

Mombrú, AW ;

Saldaña, J ;

Domínguez, L ;

Coll, J ;

Manta, E .

JOURNAL OF NATURAL PRODUCTS, 1998, 61 (12) :1560-1563

[7]

DEHMLOW EV, 1980, LIEBIGS ANN CHEM, P1

[8] Salicylihalamides A and B, novel cytotoxic macrolides from the marine sponge Haliclona sp. [J].

Erickson, KL ;

Beutler, JA ;

Cardellina, JH ;

Boyd, MR .

JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (23) :8188-8192

[9]

Fürstner A, 2001, CHEM-EUR J, V7, P5286, DOI 10.1002/1521-3765(20011217)7:24<5286::AID-CHEM5286>3.0.CO

[10]

2-G

← 1 2 3 4 →