Total synthesis of (-)-dysithiazolamide

被引：44

作者：

Arda, Ana ^{[1
]}

Soengas, Raquel G. ^{[1
]}

Nieto, M. Isabel ^{[1
]}

Jimenez, Carlos ^{[1
]}

Rodriguez, Jaime ^{[1
]}

机构：

[1] Univ A Coruna, Fac Ciencias, Dept Quim Fundamental, La Coruna 15071, Spain

来源：

ORGANIC LETTERS | 2008年 / 10卷 / 11期

关键词：

D O I：

10.1021/ol800551g

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The tetrachlorinated natural product (-)-dysithiazolamide was synthesized from L-glutamic acid in a convergent way, confirming the previously proposed (2S,4S,6S,8S) absolute stereochemistry.

引用

页码：2175 / 2178

页数：4

共 26 条

[1] NMR J-based analysis of nitrogen-containing moieties and application to dysithiazolamide, a new polychlorinated dipeptide from Dysidea sp.
Ardá, A
Rodríguez, J
Nieto, RM
Bassarello, C
Gomez-Paloma, L
Bifulco, G
Jiménez, C
[J]. TETRAHEDRON, 2005, 61 (42) : 10093 - 10098
[2] A study of polychlorinated leucine derivatives:: synthesis of (2S,4S)-5,5-dichloroleucine
Ardá, A
Jiménez, C
Rodríguez, J
[J]. TETRAHEDRON LETTERS, 2004, 45 (16) : 3241 - 3243
[3] Polychlorinated leucine derivatives:: Synthesis of (2S,4R)-5,5-dichloroleucine and its J-based analysis
Arda, Ana
Jimenez, Carlos
Rodriguez, Jaime
[J]. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2006, 2006 (16) : 3645 - 3651
[4] Mechanistic study of the reactions of 1,1-dihalo-2-methyl-2-phenylpropanes with LDA. Evidence for radical and carbene pathways
Ashby, EC
Mehdizadeh, A
Deshpande, AK
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (04) : 1322 - 1330
[5] OBSERVATIONS ON THE HANTZSCH REACTION - SYNTHESIS OF N-TBOC-S-DOLAPHENINE
BREDENKAMP, MW
HOLZAPFEL, CW
SYNMAN, RM
VANZYL, WJ
[J]. SYNTHETIC COMMUNICATIONS, 1992, 22 (21) : 3029 - 3039
[6] The barbamide biosynthetic gene cluster: a novel marine cyanobacterial system of mixed polyketide synthase (PKS)-non-ribosomal peptide synthetase (NRPS) origin involving an unusual trichloroleucyl starter unit
Chang, ZX
Flatt, P
Gerwick, WH
Nguyen, VA
Willis, CL
Sherman, DH
[J]. GENE, 2002, 296 (1-2) : 235 - 247
[7] Total synthesis of the chlorinated marine natural product dysamide B
Durow, Amanda C.
Long, G. Cliona
O'Connell, Susan J.
Willis, Christine L.
[J]. ORGANIC LETTERS, 2006, 8 (23) : 5401 - 5404
[8] Characterization of the initial enzymatic steps of barbamide biosynthesis
Flatt, Patricia M.
O'Connell, Susan J.
McPhail, Kerry L.
Zeller, Gloria
Willis, Christine L.
Sherman, David H.
Gerwick, William H.
[J]. JOURNAL OF NATURAL PRODUCTS, 2006, 69 (06): : 938 - 944
[9] Halogenation of unactivated carbon centers in natural product biosynthesis: Trichlorination of leucine during barbamide biosynthesis
Galonic, DP
Vaillancourt, FH
Walsh, CT
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (12) : 3900 - 3901
[10] [6-13C]-(2S,4S)-5-chloroleucine:: synthesis and incubation studies with cultures of the cyanobacterium, Lyngbya majuscula
Gerwick, WH
Leslie, P
Long, GC
Marquez, BL
Willis, CL
[J]. TETRAHEDRON LETTERS, 2003, 44 (02) : 285 - 288

← 1 2 3 →