Total synthesis of microcarpalide

被引:46
|
作者
Gurjar, MK [1 ]
Nagaprasad, R [1 ]
Ramana, CV [1 ]
机构
[1] Natl Chem Lab, Pune 411008, Maharashtra, India
关键词
D O I
10.1016/S0040-4039(03)00441-6
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A total synthesis of the natural product microcarpalide is described. Ring-closing metathesis of a dienic ester was used as the key step. Mannose was used as the chiral pool material for the construction of the olefinic-acid and a Sharpless asymmetric dihydroxylation reaction provided the chiral precursor for the synthesis of the olefinic-alcohol. (C) 2003 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:2873 / 2875
页数:3
相关论文
共 50 条
  • [21] TOTAL SYNTHESIS OF (+/-)-DIHYDRONORFLUOROCURARINE AND AN IMPROVED TOTAL SYNTHESIS OF (+/-)-GEISSOSCHIZOLINE
    HARLEYMA.J
    TAYLOR, CG
    JOURNAL OF THE CHEMICAL SOCIETY D-CHEMICAL COMMUNICATIONS, 1970, (13): : 812 - &
  • [22] Convergency and divergency as strategic elements in total synthesis:: The total synthesis of (-)-drupacine and the formal total synthesis of (±)-Cephalotaxine, (-)-cephalotaxine, and (+)-cephalotaxine
    Liu, Qi
    Ferreira, Eric M.
    Stoltz, Brian M.
    JOURNAL OF ORGANIC CHEMISTRY, 2007, 72 (19): : 7352 - 7358
  • [23] ASYMMETRIC TOTAL SYNTHESIS OF ERYTHROMYCIN .3. TOTAL SYNTHESIS OF ERYTHROMYCIN
    WOODWARD, RB
    LOGUSCH, E
    NAMBIAR, KP
    SAKAN, K
    WARD, DE
    AUYEUNG, BW
    BALARAM, P
    BROWNE, LJ
    CARD, PJ
    CHEN, CH
    CHENEVERT, RB
    FLIRI, A
    FROBEL, K
    GAIS, HJ
    GARRATT, DG
    HAYAKAWA, K
    HEGGIE, W
    HESSON, DP
    HOPPE, D
    HOPPE, I
    HYATT, JA
    IKEDA, D
    JACOBI, PA
    KIM, KS
    KOBUKE, Y
    KOJIMA, K
    KROWICKI, K
    LEE, VJ
    LEUTERT, T
    MALCHENKO, S
    MARTENS, J
    MATTHEWS, RS
    ONG, BS
    PRESS, JB
    RAJANBABU, TV
    ROUSSEAU, G
    SAUTER, HM
    SUZUKI, M
    TATSUTA, K
    TOLBERT, LM
    TRUESDALE, EA
    UCHIDA, I
    UEDA, Y
    UYEHARA, T
    VASELLA, AT
    VLADUCHICK, WC
    WADE, PA
    WILLIAMS, RM
    WONG, HNC
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1981, 103 (11) : 3215 - 3217
  • [24] TOTAL SYNTHESIS OF HUNTERIA ALKALOIDS - STEREOCHEMICAL CONSIDERATIONS AND A TOTAL SYNTHESIS OF (+-)-VINCAMINOL
    CASTEDO, L
    HARLEYMA.J
    LEENEY, TJ
    CHEMICAL COMMUNICATIONS, 1968, (19) : 1186 - +
  • [25] REGIOCONTROLLED TOTAL SYNTHESIS OF IMERUBRINE - THE FIRST TOTAL SYNTHESIS OF A TROPOLOISOQUINOLINE ALKALOID
    BANWELL, MG
    IRELAND, NK
    JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1994, (05) : 591 - 592
  • [26] TOTAL SYNTHESIS OF ERYTHROMYCINS .5. TOTAL SYNTHESIS OF ERYTHRONOLIDE-A
    COREY, EJ
    HOPKINS, PB
    KIM, S
    YOO, S
    NAMBIAR, KP
    FALCK, JR
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1979, 101 (23) : 7131 - 7134
  • [27] TOTAL SYNTHESIS OF STEROIDS .I. TOTAL SYNTHESIS OF RACEMIC EQUILENINE
    HOREAU, A
    LORTHIOY, E
    GUETTE, JP
    COMPTES RENDUS HEBDOMADAIRES DES SEANCES DE L ACADEMIE DES SCIENCES SERIE C, 1969, 269 (10): : 558 - &
  • [28] First stereoselective total synthesis of pectinolide C and total synthesis of pectinolide A
    Sabitha, Gowravaram
    Das, Sukant Kishore
    AnkiReddy, Praveen
    Yadav, J. S.
    TETRAHEDRON LETTERS, 2013, 54 (09) : 1097 - 1099
  • [29] STUDIES ON THE TOTAL SYNTHESIS OF OXETANOCIN .2. TOTAL SYNTHESIS OF OXETANOCIN
    NIITSUMA, S
    ICHIKAWA, Y
    KATO, K
    TAKITA, T
    TETRAHEDRON LETTERS, 1987, 28 (40) : 4713 - 4714
  • [30] TOTAL SYNTHESIS OF POLYCYCLIC TRITERPENES - TOTAL SYNTHESIS OF (+)-ALPHA-ONOCERIN
    STORK, G
    MEISELS, A
    DAVIES, JE
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1963, 85 (21) : 3419 - &