Synthesis of (-)-terpestacin via catalytic, stereoselective fragment coupling:: Siccanol is terpestacin, not 11-epi-terpestacin

被引:64
作者
Chan, J [1 ]
Jamison, TF [1 ]
机构
[1] MIT, Dept Chem, Cambridge, MA 02139 USA
关键词
D O I
10.1021/ja0373925
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
引用
收藏
页码:11514 / 11515
页数:2
相关论文
共 26 条
[1]   CONVENIENT SYNTHETIC APPROACH TO 3- AND 4-ALKYL-2,3-DIHYDROFURANS [J].
BOTTEGHI, C ;
CECCAREL.G ;
STEFANI, A ;
CONSIGLI.G .
JOURNAL OF ORGANIC CHEMISTRY, 1972, 37 (11) :1835-&
[2]   P-chiral, monodentate ferrocenyl phosphines, novel ligands for asymmetric catalysis [J].
Colby, EA ;
Jamison, TF .
JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (01) :156-166
[3]   A MECHANISTICALLY DESIGNED BIS-CINCHONA ALKALOID LIGAND ALLOWS POSITION-SELECTIVE AND ENANTIOSELECTIVE DIHYDROXYLATION OF FARNESOL AND OTHER OLIGOPRENYL DERIVATIVES AT THE TERMINAL ISOPROPYLIDENE UNIT [J].
COREY, EJ ;
NOE, MC ;
LIN, SZ .
TETRAHEDRON LETTERS, 1995, 36 (48) :8741-8744
[4]   SELECTIVE PERHYDROXYLATION OF SQUALENE - TAMING THE ARITHMETIC DEMON [J].
CRISPINO, GA ;
HO, PT ;
SHARPLESS, KB .
SCIENCE, 1993, 259 (5091) :64-66
[5]   DIASTEREOSELECTIVE AND ENANTIOSELECTIVE TOTAL SYNTHESIS OF THE HEPATOPROTECTIVE AGENT CLAUSENAMIDE [J].
HARTWIG, W ;
BORN, L .
JOURNAL OF ORGANIC CHEMISTRY, 1987, 52 (19) :4352-4358
[6]   AN EFFECTIVE AND SELECTIVE CONJUGATE PROPARGYLATION REACTION OF STANNYLALLENES TO ALPHA-BETA-UNSATURATED CARBONYL-COMPOUNDS AND ALPHA-NITRO OLEFINS [J].
HARUTA, J ;
NISHI, K ;
MATSUDA, S ;
AKAI, S ;
TAMURA, Y ;
KITA, Y .
JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (16) :4853-4859
[7]   Highly selective catalytic intermolecular reductive coupling of alkynes and aldehydes [J].
Huang, WS ;
Chan, J ;
Jamison, TF .
ORGANIC LETTERS, 2000, 2 (26) :4221-4223
[8]   TERPESTACIN, A NOVEL SYNCYTIUM FORMATION INHIBITOR, ISOLATED FROM ARTHRINIUM SPECIES [J].
IIMURA, S ;
OKA, M ;
NARITA, Y ;
KONISHI, M ;
KAKISAWA, H ;
GAO, Q ;
OKI, T .
TETRAHEDRON LETTERS, 1993, 34 (03) :493-496
[9]   Anti-angiogenic activity of terpestacin, a bicyclo sesterterpene from Embellisia chlangdospora [J].
Jung, HJ ;
Lee, HB ;
Kim, CJ ;
Rho, JR ;
Shin, JH ;
Kwon, HJ .
JOURNAL OF ANTIBIOTICS, 2003, 56 (05) :492-496
[10]   The utility of vinyl ethers and vinyl esters in the Khand reaction. The value of vinyl esters as ethylene equivalents and a modified synthesis of (+)-taylorione as an example [J].
Kerr, WJ ;
McLaughlin, M ;
Pauson, PL ;
Robertson, SM .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2001, 630 (01) :104-117