Biosynthesis inspired Diels-Alder route to pyridines: synthesis of the 2,3-dithiazolylpyridine core of the thiopeptide antibiotics

被引:62
作者
Moody, CJ [1 ]
Hughes, RA
Thompson, SP
Alcaraz, L
机构
[1] Univ Exeter, Sch Chem, Exeter EX4 4QD, Devon, England
[2] AstraZeneca, R&D Charnwood, Dept Med Chem, Loughborough LE11 5RH, Leics, England
关键词
D O I
10.1039/b204868j
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Reaction of serine derived 1-alkoxy-2-azadienes with dehydroalanine derived dienophiles results in Diels-Alder reaction and aromatisation to give 2,3,6-trisubstituted pyridines, thereby establishing the viability of the proposed biosynthetic route to the pyridine ring of the thiopeptide antibiotics originally proposed by Bycroft and Gowland.
引用
收藏
页码:1760 / 1761
页数:2
相关论文
共 27 条
[1]   STRUCTURE OF THIOSTREPTON [J].
ANDERSON, B ;
CROWFOOT.D ;
VISWAMIT.MA .
NATURE, 1970, 225 (5229) :233-&
[2]   Synthesis of 1-amino-4-hydroxycyclohexane-1-carboxylic acids [J].
Avenoza, A ;
Cativiela, C ;
Fernández-Rico, MA ;
Peregrina, JM .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1999, (22) :3375-3379
[3]   Total synthesis of the thiopeptide promothiocin A [J].
Bagley, MC ;
Bashford, KE ;
Hesketh, CL ;
Moody, CJ .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (14) :3301-3313
[4]   REACTIONS OF 3-CARBOMETHOXY-2-AZA-1,3-BUTADIENE DERIVATIVES WITH DIENOPHILES [J].
BALSAMINI, C ;
BEDINI, A ;
GALARINI, R ;
SPADONI, G ;
TARZIA, G ;
HAMDAN, M .
TETRAHEDRON, 1994, 50 (43) :12375-12394
[5]   Recent developments in imino Diels-Alder reactions [J].
Buonora, P ;
Olsen, JC ;
Oh, T .
TETRAHEDRON, 2001, 57 (29) :6099-6138
[6]   A three-step procedure for asymmetric catalytic reductive amidation of ketones [J].
Burk, MJ ;
Casy, G ;
Johnson, NB .
JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (18) :6084-6085
[7]   N-Fmoc-dehydroalanine:: a versatile molecular scaffold for the rapid solid-phase synthesis of cycloaliphatic amino acids [J].
Burkett, BA ;
Chai, CLL .
TETRAHEDRON LETTERS, 2000, 41 (34) :6661-6664
[8]   STRUCTURES OF HIGHLY MODIFIED PEPTIDE ANTIBIOTICS MICROCOCCIN P1 AND P2 [J].
BYCROFT, BW ;
GOWLAND, MS .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1978, (06) :256-258
[9]   Synthesis of the Bycroft-Gowland structure of micrococcin P1 [J].
Ciufolini, MA ;
Shen, YC .
ORGANIC LETTERS, 1999, 1 (11) :1843-1846
[10]   The constitution of micrococcin P1: the Bycroft-Gowland hypothesis confirmed [J].
Fenet, B ;
Pierre, F ;
Cundliffe, E ;
Ciufolini, MA .
TETRAHEDRON LETTERS, 2002, 43 (13) :2367-2370