Synthetic studies on thiostrepton: Construction of thiostrepton analogues with the thiazoline-containing macrocycle

被引:52
作者
Nicolaou, KC
Nevalainen, M
Zak, M
Bulat, S
Bella, M
Safina, BS
机构
[1] Scripps Res Inst, Dept Chem, La Jolla, CA 92037 USA
[2] Scripps Res Inst, Skaggs Inst Chem Biol, La Jolla, CA 92037 USA
[3] Univ Calif San Diego, Dept Chem & Biochem, La Jolla, CA 92093 USA
关键词
amino acids; antibiotics; macrocycles; natural products; thiazolines;
D O I
10.1002/anie.200351745
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Leading the way: The novel thiostrepton analogue 1 and its 5S, 6S diastereomer were synthesized through macrolactamization reactions. Forays towards the total synthesis of the natural product itself should follow a similar strategy.
引用
收藏
页码:3418 / 3424
页数:7
相关论文
共 28 条
[1]   Metal catalyzed diazo transfer for the synthesis of azides from amines [J].
Alper, PB ;
Hung, SC ;
Wong, CH .
TETRAHEDRON LETTERS, 1996, 37 (34) :6029-6032
[2]   STRUCTURE OF THIOSTREPTON [J].
ANDERSON, B ;
CROWFOOT.D ;
VISWAMIT.MA .
NATURE, 1970, 225 (5229) :233-&
[3]   Structure of the macrocycle thiostrepton solved using the anomalous dispersion contribution of sulfur [J].
Bond, CS ;
Shaw, MP ;
Alphey, MS ;
Hunter, WN .
ACTA CRYSTALLOGRAPHICA SECTION D-STRUCTURAL BIOLOGY, 2001, 57 :755-758
[4]   Stereoselective synthesis of both enantiomers of 1,4-anhydro-alditols, 1,4-anhydro-2-amino-alditols and D- and L-isonucleosides from 2,3-O-isopropylidene-D-glyceraldehyde using iodine-induced cyclization as the key step [J].
Bravo, F ;
Díaz, Y ;
Castillón, S .
TETRAHEDRON-ASYMMETRY, 2001, 12 (11) :1635-1643
[5]   DIASTEREOSELECTIVE STRECKER REACTION OF IMINES DERIVED FROM D-GLYCERALDEHYDE - A NEW ROUTE TO BETA-HYDROXY-ALPHA-AMINO ACIDS [J].
CATIVIELA, C ;
DIAZDEVILLEGAS, MD ;
GALVEZ, JA .
TETRAHEDRON LETTERS, 1995, 36 (16) :2859-2860
[6]   Synthesis of the Bycroft-Gowland structure of micrococcin P1 [J].
Ciufolini, MA ;
Shen, YC .
ORGANIC LETTERS, 1999, 1 (11) :1843-1846
[7]   High yielding synthesis of dehydroamino acid and dehydropeptide derivatives [J].
Ferreira, PMT ;
Maia, HLS ;
Monteiro, LS ;
Sacramento, J .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1999, (24) :3697-3703
[8]   Selective detachment of Boc-protected amino acids and peptides from Merrifield, PAM and Wang resins by trimethyltin hydroxide [J].
Furlán, RLE ;
Mata, EG ;
Mascaretti, OA ;
Peña, C ;
Coba, MP .
TETRAHEDRON, 1998, 54 (43) :13023-13034
[9]   Synthetic studies on the thiostrepton family of peptide antibiotics: synthesis of the tetrasubstituted dehydropiperidine and piperidine cores [J].
Higashibayashi, S ;
Hashimoto, K ;
Nakata, M .
TETRAHEDRON LETTERS, 2002, 43 (01) :105-110
[10]   STRUCTURAL BIOCHEMISTRY .23. SYNTHESIS OF THE DOLASTATIN THIAZOLE AMINO-ACID COMPONENT (GLN)THZ [J].
HOLZAPFEL, CW ;
PETTIT, GR .
JOURNAL OF ORGANIC CHEMISTRY, 1985, 50 (13) :2323-2327