Total synthesis of (-)-desoxoprosopinine via the diastereoselective reduction of homochiral2-acyl-N-Boc-oxazolidines

被引：40
作者：
Agami, C [1 ]
Couty, F [1 ]
Mathieu, H [1 ]
机构：
[1] Univ Pierre & Marie Curie, CNRS, Lab Synth Asymetr, F-75005 Paris, France
来源：
TETRAHEDRON LETTERS | 1998年 / 39卷 / 21期
关键词：
oxazolidines; alkaloids; asymmetric synthesis;
D O I：
10.1016/S0040-4039(98)00646-7
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
(-)-Desoxoprosopinine was synthesised from (R)-phenylglycinol as the chiral source. The three distinct steps used for the construction of the three stereogenic centers of the target were all highly diastereoselective. These steps include a reduction of a homochiral N-Boc-2-acyl oxazolidine and the stereoselectivity of this reaction can be explained by a non chelated model. An original N-debenzylation of the phenyl glycinol appendage was devised in this synthesis. (C) 1998 Published by Elsevier Science Ltd. All rights reserved.
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收藏
页码：3505 / 3508
页数：4
相关论文
共 14 条
  • [1] N-BOC 2-ACYLOXAZOLIDINES - USEFUL PRECURSORS TO ENANTIOPURE 1,2-DIOLS VIA HIGHLY DIASTEREOSELECTIVE NUCLEOPHILIC ADDITIONS
    AGAMI, C
    COUTY, F
    LEQUESNE, C
    [J]. TETRAHEDRON, 1995, 51 (14) : 4043 - 4056
  • [2] AGAMI C, 1996, TETRAHEDRON LETT, V37, P4000
  • [3] ANH NT, 1977, NOUV J CHIM, V1, P61
  • [4] CHEREST M, 1968, TETRAHEDRON LETT, V9, P2199
  • [5] CONSTRUCTION OF HYDROXYLATED ALKALOIDS (+/-)-MANNONOLACTAM, (+/-)-DEOXYMANNOJIRIMYCIN, AND (+/-)-PROSOPININE THROUGH AZA-ANNULATION
    COOK, GR
    BEHOLZ, LG
    STILLE, JR
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (13) : 3575 - 3584
  • [6] FRIEBOES KC, 1993, SYNLETT, P921
  • [7] CHIRAL 1,4-DIHYDROPYRIDINE EQUIVALENTS - A NEW APPROACH TO THE ASYMMETRIC-SYNTHESIS OF ALKALOIDS - THE ENANTIOSPECIFIC SYNTHESIS OF (+)-CONIINE AND (-)-CONIINE AND DIHYDROPINIDINE
    GUERRIER, L
    ROYER, J
    GRIERSON, DS
    HUSSON, HP
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1983, 105 (26) : 7754 - 7755
  • [8] Total synthesis of (+)-desoxoprosopinine via the intramolecular reaction of gamma-aminoallylstannane
    Kadota, I
    Kawada, M
    Muramatsu, Y
    Yamamoto, Y
    [J]. TETRAHEDRON LETTERS, 1997, 38 (42) : 7469 - 7470
  • [9] KHUONGHUU Q, 1972, B SOC CHIM BELG, V81, P425
  • [10] STEREOCHEMISTRY OF PALYTOXIN .1. C85-C115 SEGMENT
    KLEIN, LL
    MCWHORTER, WW
    KO, SS
    PFAFF, KP
    KISHI, Y
    UEMURA, D
    HIRATA, Y
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1982, 104 (25) : 7362 - 7364
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