Diastereoselective synthesis of protected syn 1,3-diols:: Preparation of the C16-C24 portion of dolabelides

被引:30
作者
Grimaud, L
de Mesmay, R
Prunet, J [1 ]
机构
[1] Ecole Polytech, DCSO, CNRS, UMR 7652,Lab Synth Organ, F-91128 Palaiseau, France
[2] Ecole Natl Super Tech Avancees, Lab Chim & Proc, F-75015 Paris, France
关键词
D O I
10.1021/ol017122w
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
We have designed a new method to make synthons encompassing a protected syn 1,3-diol motif and an aldehyde a to the 1,3-dioxane ring. An additional stereocenter was also created, potentially leading to stereochemically defined 1,2,4-triols. This method was successfully applied to the synthesis of the C16-C24 portion of Dolabelides.
引用
收藏
页码:419 / 421
页数:3
相关论文
共 16 条
[1]  
Berque I, 1998, SYNLETT, P1132
[2]   DIASTEREOSELECTIVE SYNTHESIS OF PROTECTED SYN 1,3-DIOLS BY BASE-CATALYZED INTRAMOLECULAR CONJUGATE ADDITION OF HEMIACETAL-DERIVED ALKOXIDE NUCLEOPHILES [J].
EVANS, DA ;
GAUCHETPRUNET, JA .
JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (09) :2446-2453
[3]   A MILD OXIDIZING REAGENT FOR ALCOHOLS AND 1,2-DIOLS - O-IODOXYBENZOIC ACID (IBX) IN DMSO [J].
FRIGERIO, M ;
SANTAGOSTINO, M .
TETRAHEDRON LETTERS, 1994, 35 (43) :8019-8022
[4]   OXIDATION OF ALCOHOLS WITH O-IODOXYBENZOIC ACID (IBX) IN DMSO - A NEW INSIGHT INTO AN OLD HYPERVALENT IODINE REAGENT [J].
FRIGERIO, M ;
SANTAGOSTINO, M ;
SPUTORE, S ;
PALMISANO, G .
JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (22) :7272-7276
[5]   HIGHLY DIASTEREOSELECTIVE SYNTHESIS OF 1,2-EPOXY-4-HYDROXYALKYL CARBAMATES - MASKED AND ACTIVATED ALPHA,GAMMA-DIHYDROXY-ALKANALS AND ALPHA,GAMMA-DIHYDROXY-ALKANONES [J].
HOPPE, D ;
LUSSMANN, J ;
JONES, PG ;
SCHMIDT, D ;
SHELDRICK, GM .
TETRAHEDRON LETTERS, 1986, 27 (31) :3591-3594
[6]  
HOPPE D, 1989, SYNTHESIS-STUTTGART, P83
[7]   METALLATED NITROGEN DERIVATIVES OF CARBONIC-ACID IN ORGANIC-SYNTHESIS .27. HOMOALDOL REACTION .7. LITHIATION OF ACYCLIC 2-ALKENYL N,N-DIALKYLCARBAMATES - SILYLATION AND GAMMA-SELECTIVE ALPHA-HYDROXYALKYLATION OF HOMOENOLATE REAGENTS [J].
HOPPE, D ;
HANKO, R ;
BRONNEKE, A ;
LICHTENBERG, F ;
VANHULSEN, E .
CHEMISCHE BERICHTE-RECUEIL, 1985, 118 (07) :2822-2851
[8]  
Hoppe D, 1997, SYNTHESIS-STUTTGART, P183
[9]   HIGH-FIELD FT NMR APPLICATION OF MOSHER METHOD - THE ABSOLUTE-CONFIGURATIONS OF MARINE TERPENOIDS [J].
OHTANI, I ;
KUSUMI, T ;
KASHMAN, Y ;
KAKISAWA, H .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (11) :4092-4096
[10]   DOLABELIDE-A AND DOLABELIDE-B, CYTOTOXIC-22-MEMBERED MACROLIDES ISOLATED FROM THE SEA HARE DOLABELLA-AURICULARIA [J].
OJIKA, M ;
NAGOYA, T ;
YAMADA, K .
TETRAHEDRON LETTERS, 1995, 36 (41) :7491-7494