Synthesis of 6-vinyl and 5-vinylproline analogues of ascomycin

被引：9

作者：

Bulusu, MARC ^{[1
]}

Waldstätten, P ^{[1
]}

Tricotet, T ^{[1
]}

Rochais, C ^{[1
]}

Steck, A ^{[1
]}

Bacher, M ^{[1
]}

机构：

[1] Novartis Inst Biomed Res, A-1235 Vienna, Austria

来源：

TETRAHEDRON LETTERS | 2004年 / 45卷 / 30期

关键词：

phototransformation; macrolactam; 5-vinylproline; 6-vinyl ascomycin;

D O I：

10.1016/j.tetlet.2004.06.010

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

6-Vinyl (12) and (5R)- and (5S)-vinylproline (18, 19) analogues of ascomycin are synthesised starting from the known suitably protected (6S)-methoxy-9-hydroxy derivative (4) of ascomycin. The strategy involves hydrolytic cleavage of the C-epsilon-N bond of the pipecolic acid moiety, extension of the amino acid side chain by two or one carbon units, functional group manipulations, Pd-catalysed reinstallation of the C-epsilon-N or C-delta-N bonds, followed by deprotection and oxidation. (C) 2004 Elsevier Ltd. All rights reserved.

引用

页码：5833 / 5836

页数：4

共 18 条

[1] ARAI T, 1962, J ANTIBIOT, V15, P231
[2] SYNTHESIS OF THE NOVEL SARCOSINE AND PROLINE (FK-525) ANALOGS OF FK-506 - REARRANGEMENT OF THE ALLYLIC ESTER SYSTEM
ASKIN, D
REAMER, RA
JOE, D
VOLANTE, RP
SHINKAI, I
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (20) : 5448 - 5450
[3] EFFICIENT DEGRADATION OF FK-506 TO A VERSATILE SYNTHETIC INTERMEDIATE
ASKIN, D
JOE, D
REAMER, RA
VOLANTE, RP
SHINKAI, I
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (20) : 5451 - 5454
[4] Bulusu A.R.C.M., 1994, Eur Pat Appl, Patent No. [0626385, EP 626385, 626385]
[5] Selective photochemical cleavage of an α-ketoamide in a highly functionalised macrolide ascomycin
Bulusu, MARC
Waldstätten, P
Tricotett, T
Schulz, G
[J]. TETRAHEDRON LETTERS, 2004, 45 (12) : 2527 - 2530
[6] Novel analogues of ascomycin with modifications in the amino acid unit through photochemistry:: the synthesis of 5,6-dehydroascomycin, SDZ ASQ 871
Bulusu, MARC
Waldstätten, P
Schulz, G
Grassberger, M
[J]. TETRAHEDRON LETTERS, 2004, 45 (12) : 2523 - 2526
[7] Bulusu MARC, 1999, INDIAN J CHEM B, V38, P1159
[8] READILY ACCESSIBLE 12-I-5 OXIDANT FOR THE CONVERSION OF PRIMARY AND SECONDARY ALCOHOLS TO ALDEHYDES AND KETONES
DESS, DB
MARTIN, JC
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1983, 48 (22) : 4155 - 4156
[9] Elidel (pimecrolimus) cream 1%: A nonsteroidal topical agent for the treatment of atopic dermatitis
Eichenfield, LF
Beck, L
[J]. JOURNAL OF ALLERGY AND CLINICAL IMMUNOLOGY, 2003, 111 (05) : 1154 - 1168
[10] Graham-Brown RAC, 2003, INT J CLIN PRACT, V57, P319

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