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AN EXPEDITIOUS SYNTHESIS OF THE C(1)-C(14) SUBUNIT OF HALICHONDRIN-B

被引：49
作者：
BURKE, SD
JUNG, KW
PHILLIPS, JR
PERRI, RE
机构：
[1] Department of Chemistry, University of Wisconsin-Madison, Madison
来源：
TETRAHEDRON LETTERS | 1994年 / 35卷 / 05期
基金：
美国国家卫生研究院;
关键词：
PINACOL REARRANGEMENT; INTRAMOLECULAR MICHAEL ADDITION; HALICHONDRIN B SUBUNIT;
D O I：
10.1016/S0040-4039(00)75795-9
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The synthesis of the C(1)-C(14) segment 1 of hahchondrin B was achieved efficiently. Featured are the pinacol rearrangement of alpha-hydroxymesylate 9, the intramolecular Michael addition of 11, and the one-pot multistep conversion of 13 to 1.
引用
收藏
页码：703 / 706
页数：4
相关论文
共 33 条
  • [1] TOTAL SYNTHESIS OF HALICHONDRIN-B AND NORHALICHONDRIN-B
    AICHER, TD
    BUSZEK, KR
    FANG, FG
    FORSYTH, CJ
    JUNG, SH
    KISHI, Y
    MATELICH, MC
    SCOLA, PM
    SPERO, DM
    YOON, SK
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (08) : 3162 - 3164
  • [2] SYNTHETIC STUDIES TOWARDS HALICHONDRINS - SYNTHESIS OF THE C.27-C.38 SEGMENT
    AICHER, TD
    BUSZEK, KR
    FANG, FG
    FORSYTH, CJ
    JUNG, SH
    KISHI, Y
    SCOLA, PM
    [J]. TETRAHEDRON LETTERS, 1992, 33 (12) : 1549 - 1552
  • [3] SYNTHETIC STUDIES TOWARDS HALICHONDRINS
    AICHER, TD
    KISHI, Y
    [J]. TETRAHEDRON LETTERS, 1987, 28 (30) : 3463 - 3466
  • [4] BAI R, 1991, J BIOL CHEM, V266, P15882
  • [5] REAKTIONEN MIT PHOSPHIN-ALKYLENEN .2. C-ACYLIERUNG VON PHOSPHIN-ALKYLENEN - EIN NEUER WEG ZUR SYNTHESE VON KETONEN
    BESTMANN, HJ
    ARNASON, B
    [J]. CHEMISCHE BERICHTE-RECUEIL, 1962, 95 (06): : 1513 - &
  • [6] BOYD MR, COMMUNICATION
  • [7] SYNTHESIS OF A C(22)-]C(34) HALICHONDRIN PRECURSOR VIA A DOUBLE DIOXANONE-TO-DIHYDROPYRAN REARRANGEMENT
    BURKE, SD
    BUCHANAN, JL
    ROVIN, JD
    [J]. TETRAHEDRON LETTERS, 1991, 32 (32) : 3961 - 3964
  • [8] SYNTHETIC STUDIES TOWARDS HALICHONDRINS - SYNTHESIS OF THE LEFT HALF OF HALICHONDRINS
    BUSZEK, KR
    FANG, FG
    FORSYTH, CJ
    JUNG, SH
    KISHI, Y
    SCOLA, PM
    YOON, SK
    [J]. TETRAHEDRON LETTERS, 1992, 33 (12) : 1553 - 1556
  • [9] PREPARATION OF ENANTIOMERICALLY ENRICHED ALPHA-HYDROXY ACID-DERIVATIVES FROM ALPHA-ALKOXYORGANOSTANNANES
    CHAN, PCM
    CHONG, JM
    [J]. TETRAHEDRON LETTERS, 1990, 31 (14) : 1985 - 1988
  • [10] ASYMMETRIC REDUCTION OF ACYLSTANNANES - PREPARATION OF ENANTIOMERICALLY ENRICHED ALPHA-ALKOXYSTANNANES
    CHAN, PCM
    CHONG, JM
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (23) : 5584 - 5586
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