Synthesis and structure of tolyporphin a O,O-diacetate

被引:61
作者
Wang, WG [1 ]
Kishi, Y [1 ]
机构
[1] Harvard Univ, Dept Chem & Biol Chem, Cambridge, MA 02138 USA
关键词
D O I
10.1021/ol9902374
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
[GRAPHICS] The revised structure of tolyporphin A O,O-diacetate (2b) was synthesized by assembling fragments 4, 5, and 12, The synthetic substance was found to be identical to the O,O-diacetate derived from natural tolyporphin A in every respect, thus establishing the relative and absolute configurations of this natural product.
引用
收藏
页码:1129 / 1132
页数:4
相关论文
共 10 条
[1]   BIOCHEMISTRY OF MULTIDRUG-RESISTANCE MEDIATED BY THE MULTIDRUG TRANSPORTER [J].
GOTTESMAN, MM ;
PASTAN, I .
ANNUAL REVIEW OF BIOCHEMISTRY, 1993, 62 :385-427
[2]   Extension of the eschenmoser sulfide contraction iminoester cyclization method to the synthesis of tolyporphin chromophore [J].
Minehan, TG ;
Kishi, Y .
TETRAHEDRON LETTERS, 1997, 38 (39) :6811-6814
[3]  
Minehan TG, 1999, ANGEW CHEM INT EDIT, V38, P923, DOI 10.1002/(SICI)1521-3773(19990401)38:7<923::AID-ANIE923>3.0.CO
[4]  
2-7
[5]   beta-selective C-glycosidations: Lewis-acid mediated reactions of carbohydrates with silyl ketene acetals [J].
Minehan, TG ;
Kishi, Y .
TETRAHEDRON LETTERS, 1997, 38 (39) :6815-6818
[6]  
Minehan TG, 1999, ANGEW CHEM INT EDIT, V38, P926, DOI 10.1002/(SICI)1521-3773(19990401)38:7<926::AID-ANIE926>3.0.CO
[7]  
2-W
[8]   TOLYPORPHIN, A NOVEL MULTIDRUG RESISTANCE REVERSING AGENT FROM THE BLUE-GREEN-ALGA TOLYPOTHRIX-NODOSA [J].
PRINSEP, MR ;
CAPLAN, FR ;
MOORE, RE ;
PATTERSON, GML ;
SMITH, CD .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (01) :385-387
[9]   SYNTHESIS OF ENANTIOMERS OF 4-SUBSTITUTED GAMMA-LACTONES WITH KNOWN ABSOLUTE-CONFIGURATION [J].
RAVID, U ;
SMITH, LR ;
SILVERSTEIN, RM .
TETRAHEDRON, 1978, 34 (10) :1449-1452
[10]   CELL BIOLOGICAL MECHANISMS OF MULTIDRUG-RESISTANCE IN TUMORS [J].
SIMON, SM ;
SCHINDLER, M .
PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 1994, 91 (09) :3497-3504