Stereoselective Total Synthesis of (-)-(6R,11R,14R)-Colletallol via RCM Protocol

被引:6
作者
Krishna, Palakodety Radha [1 ]
Ramana, D. Venkata [1 ]
Reddy, B. Karunakar [1 ]
机构
[1] Indian Inst Chem Technol, Div Organ Chem 3, Discovery Lab, Hyderabad 500607, Andhra Pradesh, India
关键词
(-)-colletallol; ring-closing metathesis (RCM); Grubbs II catalyst; Jacobsen's hydrolytic kinetic resolution (HKR); ENANTIOSELECTIVE TOTAL-SYNTHESIS; KINETIC RESOLUTION; TERMINAL EPOXIDES; COLLETODIOL;
D O I
10.1055/s-0029-1218270
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The total synthesis of' (-)-colletallol via a ring-closing metathesis protocol is reported.
引用
收藏
页码:2924 / 2926
页数:3
相关论文
共 24 条
[1]   NOVEL CONVERSION OF EPOXIDES TO ONE-CARBON HOMOLOGATED ALLYLIC ALCOHOLS BY DIMETHYLSULFONIUM METHYLIDE [J].
ALCARAZ, L ;
HARNETT, JJ ;
MIOSKOWSKI, C ;
MARTEL, JP ;
LEGALL, T ;
SHIN, DS ;
FALCK, JR .
TETRAHEDRON LETTERS, 1994, 35 (30) :5449-5452
[2]   Enantioselective total synthesis of the (-)-(6R,11R,14S)-isomer of colletallol [J].
Amigoni, SJ ;
Toupet, LJ ;
LeFloch, YJ .
JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (18) :6374-6378
[3]  
Chatterjee AK, 2002, ANGEW CHEM INT EDIT, V41, P3171, DOI 10.1002/1521-3773(20020902)41:17<3171::AID-ANIE3171>3.0.CO
[4]  
2-O
[5]   Synthesis of oxygen- and nitrogen-containing heterocycles by ring-closing metathesis [J].
Deiters, A ;
Martin, SF .
CHEMICAL REVIEWS, 2004, 104 (05) :2199-2238
[6]   AN ENANTIOSELECTIVE TOTAL SYNTHESIS OF THE MACRODIOLIDE (-)-(RRR)-COLLETALLOL [J].
DOMMERHOLT, FJ ;
THIJS, L ;
ZWANENBURG, B .
TETRAHEDRON LETTERS, 1991, 32 (11) :1495-1498
[7]   MILD CLEAVAGE OF METHOXYMETHYL (MOM) ETHERS WITH TRIMETHYLSILYL BROMIDE [J].
HANESSIAN, S ;
DELORME, D ;
DUFRESNE, Y .
TETRAHEDRON LETTERS, 1984, 25 (24) :2515-2518
[8]   The first synthesis of a 12-membered macrolide natural product via a RCM protocol: determination of absolute stereochemistry [J].
Krishna, Palakodety Radha ;
Srinivas, Ravula .
TETRAHEDRON-ASYMMETRY, 2008, 19 (09) :1153-1160
[9]   Stereoselective synthesis of (6S)-5,6-dihydro-6-[(2R)-2-hydroxy-6-phenylhexyl]-2H-pyran-2-one [J].
Krishna, Palakodety Radha ;
Srinivas, Ravula .
TETRAHEDRON-ASYMMETRY, 2007, 18 (18) :2197-2200
[10]   Studies directed towards the stereoselective total synthesis of ilexlactone via a tandem ring-closing enyne metathesis protocol [J].
Krishna, Palakodety Radha ;
Narsingam, M. .
TETRAHEDRON LETTERS, 2007, 48 (49) :8721-8724