Towards the Total Synthesis of Pl-3: Preparation of the Eastern Fragment through a Diastereoselective SmI2-Mediated Reformatsky Reaction

被引：17
作者：
Fuerst, Rita [1 ]
Lentsch, Christoph [1 ]
Rinner, Uwe [1 ]
机构：
[1] Univ Vienna, Dept Organ Chem, A-1090 Vienna, Austria
来源：
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2013年 / 2013卷 / 12期
关键词：
Natural products; Terpenoids; Samarium; Diastereoselectivity; Multidrug resistance; RESISTANCE REVERSING ACTIVITY; JATROPHANE DITERPENES; MOUSE LYMPHOMA; DERIVATIVES; INHIBITORS; PLANTS;
D O I：
10.1002/ejoc.201300148
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The jatrophane diterpene Pl-3, isolated in 2003 from Euphorbia platyphyllos, is a structurally complex natural product with highly promising biological properties that include pronounced antiproliferative activity and the inhibition of the efflux-pump activity of multidrug resistance p-glycoprotein. Herein, the synthesis of the eastern fragment of Pl-3 is outlined. The target compound is synthesized in nine synthetic operations in good overall yield, starting from readily available D-ribose. The key step in the preparation of the eastern part of Pl-3 is a diastereoselective SmI2-mediated Reformatsky reaction. The proposed route is highly flexible and could also be applied to the synthesis of structurally related jatrophane diterpenes.
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收藏
页码：2293 / 2297
页数：5
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共 34 条
  • [1] METAL-ASSISTED ALDOL CONDENSATION OF CHIRAL ALPHA-HALOGENATED IMIDE ENOLATES - A STEREOCONTROLLED CHIRAL EPOXIDE SYNTHESIS
    ABDELMAGID, A
    PRIDGEN, LN
    EGGLESTON, DS
    LANTOS, I
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1986, 108 (15) : 4595 - 4602
  • [2] Activity of adenosine deaminase (ADA) and adenylate deaminase (AMPDA) towards 6-chloropurine nucleosides modified in the ribose moiety
    Ciuffreda, P
    Buzzi, B
    Alessandrini, L
    Santaniello, E
    [J]. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2004, 2004 (21) : 4405 - 4409
  • [3] Jatrophane diterpenes as P-glycoprotein inhibitors. First insights of structure-activity relationships and discovery of a new, powerful lead
    Corea, G
    Fattorusso, E
    Lanzotti, V
    Taglialatela-Scafati, O
    Appendino, G
    Ballero, M
    Simon, PN
    Dumontet, C
    Di Pietro, A
    [J]. JOURNAL OF MEDICINAL CHEMISTRY, 2003, 46 (15) : 3395 - 3402
  • [4] Jatrophane diterpenes from Euphorbia spp. as modulators of multidrug resistance in cancer therapy
    Corea, G.
    Di Pietro, A.
    Dumontet, C.
    Fattorusso, E.
    Lanzotti, V.
    [J]. PHYTOCHEMISTRY REVIEWS, 2009, 8 (02) : 431 - 447
  • [5] Ti-catalyzed Reformatsky-type coupling between α-halo, ketones and aldehydes
    Estevez, Rosa E.
    Paradas, Miguel
    Millan, Alba
    Jimenez, Tania
    Robles, Rafael
    Cuerva, Juan M.
    Oltra, J. Enrique
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2008, 73 (04) : 1616 - 1619
  • [6] Asymmetric Samarium-Reformatsky reaction of chiral α-bromoacetyl-2-oxazolidinones with aldehydes
    Fukuzawa, S
    Matsuzawa, H
    Yoshimitsu, S
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (06) : 1702 - 1706
  • [7] Plants used against cancer - an extension of the work of Jonathan Hartwell
    Graham, JG
    Quinn, ML
    Fabricant, DS
    Farnsworth, NR
    [J]. JOURNAL OF ETHNOPHARMACOLOGY, 2000, 73 (03) : 347 - 377
  • [8] TOTAL SYNTHESIS OF (+/-)-EPI-JATROPHONE AND (+/-)-JATROPHONE USING PALLADIUM-CATALYZED CARBONYLATIVE COUPLING OF VINYL TRIFLATES WITH VINYLSTANNANES AS THE MACROCYCLE-FORMING STEP
    GYORKOS, AC
    STILLE, JK
    HEGEDUS, LS
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (23) : 8465 - 8472
  • [9] TOTAL SYNTHESIS OF (+)-JATROPHONE
    HAN, Q
    WIEMER, DF
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (20) : 7692 - 7697
  • [10] A NEW METHOD FOR THE SYNTHESIS OF BETA-HYDROXYESTERS BY USING METALLIC TIN
    HARADA, T
    MUKAIYAMA, T
    [J]. CHEMISTRY LETTERS, 1982, (02) : 161 - 164
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