THE FIRST CONVERGENT SYNTHESIS OF 1-ALPHA,24(R)-DIHYDROXYVITAMIN D-3 VIA DIASTEREOSELECTIVE ISOPROPYLATION AND ALKYLATIVE ENYNE CYCLIZATION

被引:16
|
作者
OKAMOTO, M [1 ]
FUJII, T [1 ]
TANAKA, T [1 ]
机构
[1] TEIJIN LTD,CHEM MFG PLANT,IWAKUNI PHARMACEUT FACTORY,IWAKUNI,YAMAGUCHI 740,JAPAN
关键词
D O I
10.1016/0040-4020(95)00243-2
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
An efficient covergent synthesis of 1 alpha,24(R)-dihydroxyvitamin D-3 (1) has been achieved using the palladium-catalyzed alkylative enyne cyclization reaction. This is the first example of the convergent coupling procedure to synthesize 1 alpha,24(R)-dihydroxyvitamin D-3 (1). The CD-ring synthons were successfully obtained via the diastereoselective addition of diisopropylzinc to CD-ring 24-aldehyde precursors in the presence of a chiral beta-amino alcohol with high diastereoselectivities
引用
收藏
页码:5543 / 5556
页数:14
相关论文
共 50 条
  • [41] Synthesis, stereochemistry, and biological activity of 1 alpha,23,25-trihydroxy-24-oxovitamin D-3, a major natural metabolite of 1 alpha,25-dihydroxyvitamin D-3
    Lee, NE
    Reddy, GS
    Brown, AJ
    Williard, PG
    BIOCHEMISTRY, 1997, 36 (31) : 9429 - 9437
  • [42] INTRINSIC BIOLOGICAL-ACTIVITIES BY 1-ALPHA,24-DIHYDROXYVITAMIN-D3 IN THE RAT
    ISHIZUKA, S
    BANNAI, K
    NARUCHI, T
    HASHIMOTO, Y
    BIOCHEMICAL AND BIOPHYSICAL RESEARCH COMMUNICATIONS, 1979, 90 (03) : 904 - 910
  • [43] THE BINDING-PROPERTIES, WITH BLOOD PROTEINS, AND TISSUE DISTRIBUTION OF 22-OXA-1-ALPHA,25-DIHYDROXYVITAMIN D-3, A NONCALCEMIC ANALOG OF 1-ALPHA,25-DIHYDROXYVITAMIN D-3, IN RATS
    KOBAYASHI, T
    TSUGAWA, N
    OKANO, T
    MASUDA, S
    TAKEUCHI, A
    KUBODERA, N
    NISHII, Y
    JOURNAL OF BIOCHEMISTRY, 1994, 115 (03): : 373 - 380
  • [44] 1-ALPHA,25-DIHYDROXYVITAMIN D-3 ANALOGS FEATURING AROMATIC AND HETEROAROMATIC RINGS - DESIGN, SYNTHESIS, AND PRELIMINARY BIOLOGICAL TESTING
    POSNER, GH
    LI, ZG
    WHITE, MC
    VINADER, V
    TAKEUCHI, K
    GUGGINO, SE
    DOLAN, P
    KENSLER, TW
    JOURNAL OF MEDICINAL CHEMISTRY, 1995, 38 (22) : 4529 - 4537
  • [45] ON THE SIDE-CHAIN CONFORMATION OF 1-ALPHA,25-DIHYDROXYVITAMIN D-3 RESPONSIBLE FOR BINDING TO THE RECEPTOR
    YAMAMOTO, K
    OHTA, M
    DELUCA, HF
    YAMADA, S
    BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1995, 5 (09) : 979 - 984
  • [46] SYNTHESIS OF 1-ALPHA,25-DIHYDROXYVITAMIN-D3 AND A-RING ANALOGS
    POSNER, GH
    KINTER, CM
    NELSON, TD
    KLUNDER, JM
    NIKOLAIDES, N
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1990, 200 : 137 - ORGN
  • [47] MODULATION OF ECTO-NUCLEOSIDE TRIPHOSPHATE PYROPHOSPHATASE ACTIVITY OF HUMAN OSTEOBLAST-LIKE BONE-CELLS BY 1-ALPHA,25-DIHYDROXYVITAMIN D-3, 24R,25-DIHYDROXYVITAMIN D-3, PARATHYROID-HORMONE, AND DEXAMETHASONE
    OYAJOBI, BO
    RUSSELL, RGG
    CASWELL, AM
    JOURNAL OF BONE AND MINERAL RESEARCH, 1994, 9 (08) : 1259 - 1266
  • [48] FACILE STEREOSELECTIVE SYNTHESIS OF (23S,25R)-1-ALPHA,25-DIHYDROXYVITAMIN-D3 26,23-LACTONE, A MAJOR METABOLITE OF 1-ALPHA,25-DIHYDROXYVITAMIN-D3
    YAMAMOTO, K
    SHIMIZU, M
    YAMADA, S
    IWATA, S
    HOSHINO, O
    JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (01): : 33 - 39
  • [49] EFFECTS OF 1-ALPHA,25-DIHYDROXYVITAMIN-D3 AND 24R,25-DIHYDROXYVITAMIN-D3 ON ALUMINUM-INDUCED RICKETS IN GROWING UREMIC RATS
    VUKICEVIC, S
    KREMPIEN, B
    STAVLJENIC, A
    JOURNAL OF BONE AND MINERAL RESEARCH, 1987, 2 (06) : 533 - 545
  • [50] RAT INTESTINAL 25-HYDROXYVITAMIN D3-DIHYDROXYVITAMIN AND 1-ALPHA,25-DIHYDROXYVITAMIN D3-24-HYDROXYLASE
    KUMAR, R
    SCHNOES, HK
    DELUCA, HF
    JOURNAL OF BIOLOGICAL CHEMISTRY, 1978, 253 (11) : 3804 - 3809