ASYMMETRIC TOTAL SYNTHESIS OF (+)-JASPLAKINOLIDE

被引:95
作者
CHU, KS [1 ]
NEGRETE, GR [1 ]
KONOPELSKI, JP [1 ]
机构
[1] UNIV CALIF SANTA CRUZ,DEPT CHEM & BIOCHEM,SANTA CRUZ,CA 95064
关键词
D O I
10.1021/jo00017a037
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A convergent synthesis of the marine cyclodepsipeptide (+)-jasplakinolide has been realized. The synthesis of the required (R)-beta-tyrosine unit is accomplished via the stereospecific palladium-catalyzed arylation of an enantiomerically pure dihydropyrimidinone. The overall yield of the synthesis, based on the longest linear sequence, is 6.6%.
引用
收藏
页码:5196 / 5202
页数:7
相关论文
共 30 条
[21]  
LIPTON MF, 1980, J ORGANOMET CHEM, V186, P155
[22]   ASYMMETRIC ALKYLATIONS OF N-ACYLDIHYDROPYRIMIDINONES [J].
NEGRETE, GR ;
KONOPELSKI, JP .
TETRAHEDRON-ASYMMETRY, 1991, 2 (02) :105-108
[23]   BIOSYNTHESIS OF AMINO-ACIDS - INVESTIGATION OF THE MECHANISM OF BETA-TYROSINE FORMATION [J].
PARRY, RJ ;
KURYLOBOROWSKA, Z .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1980, 102 (02) :836-837
[24]   INTRAMOLECULAR GENERAL ACID AND GENERAL BASE CATALYZES IN THE HYDROLYSIS OF 2-HALOTRYPTOPHANS AND THEIR ANALOGS [J].
PHILLIPS, RS ;
COHEN, LA .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1986, 108 (08) :2023-2030
[25]  
POLITZER IR, 1988, ORG SYNTH, V4, P905
[26]   TOTAL SYNTHESES OF JASPAMIDE (JASPLAKINOLIDE) AND GEODIAMOLIDE-A AND GEODIAMOLIDE-B .1. STEREOSELECTIVE SYNTHESIS OF (2S,4E,6R,8S)-8-HYDROXY-2,4,6-TRIMETHYL-4-NONENOIC ACID [J].
SCHMIDT, U ;
SIEGEL, W ;
MUNDINGER, K .
TETRAHEDRON LETTERS, 1988, 29 (11) :1269-1270
[27]   COLORED INDICATORS FOR SIMPLE DIRECT TITRATION OF MAGNESIUM AND LITHIUM REAGENTS [J].
WATSON, SC ;
EASTHAM, JF .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1967, 9 (01) :165-&
[28]   TOTAL SYNTHESIS OF GEODIAMOLIDE-A, A NOVEL CYCLODEPSIPEPTIDE OF MARINE ORIGIN [J].
WHITE, JD ;
AMEDIO, JC .
JOURNAL OF ORGANIC CHEMISTRY, 1989, 54 (04) :736-738
[29]   JASPAMIDE, A MODIFIED PEPTIDE FROM A JASPIS SPONGE, WITH INSECTICIDAL AND ANTIFUNGAL ACTIVITY [J].
ZABRISKIE, TM ;
KLOCKE, JA ;
IRELAND, CM ;
MARCUS, AH ;
MOLINSKI, TF ;
FAULKNER, DJ ;
XU, CF ;
CLARDY, JC .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1986, 108 (11) :3123-3124
[30]   PALLADIUM-CATALYZED VINYLIC SUBSTITUTION WITH HIGHLY ACTIVATED ARYL HALIDES [J].
ZIEGLER, CB ;
HECK, RF .
JOURNAL OF ORGANIC CHEMISTRY, 1978, 43 (15) :2941-2946