ENANTIOSELECTIVE SYNTHESIS OF A HALICHONDRIN-B C(20)-]C(36) PRECURSOR

被引：19
作者：
BURKE, SD
ZHANG, G
BUCHANAN, JL
机构：
[1] Department of Chemistry, University of Wisconsin-Madison, Madison
来源：
TETRAHEDRON LETTERS | 1995年 / 36卷 / 39期
基金：
美国国家卫生研究院;
关键词：
D O I：
10.1016/0040-4039(95)01454-P
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Differential functionalization of the nearly symmetrical bis(dihydropyran)3 is described leading to the C(20)-->C(36) holichondrin B precursor 1. Double hydroboration, regioselective mono-protection of the resulting diol and two-directional chain extension are featured
引用
收藏
页码：7023 / 7026
页数：4
相关论文
共 42 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] BOYD MR, COMMUNICATION
  • [6] BROEKEMA RJ, 1975, RECL TRAV CHIM PAY B, V94, P209
  • [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] AN EXPEDITIOUS SYNTHESIS OF THE C(1)-C(14) SUBUNIT OF HALICHONDRIN-B
    BURKE, SD
    JUNG, KW
    PHILLIPS, JR
    PERRI, RE
    [J]. TETRAHEDRON LETTERS, 1994, 35 (05) : 703 - 706
  • [9] 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
  • [10] STUDIES ON THE SYNTHESIS OF GLOEOSPORONE - SYNTHESIS OF THE PROPOSED 2,8-DISUBSTITUTED OXOCANE STRUCTURE
    CARLING, RW
    HOLMES, AB
    [J]. TETRAHEDRON LETTERS, 1986, 27 (50) : 6133 - 6136
12345