Synthetic studies towards phorboxazole B: Stereoselective synthesis of the C3-C19 bis-oxane oxazole fragment

被引:6
|
作者
Zhang, DH [1 ]
Zhou, WS [1 ]
机构
[1] Shanghai Inst Organ Chem, Shanghai 200032, Peoples R China
关键词
enantioselective synthesis; phorboxazole; reduction; Mukaiyama reaction; Williamson reaction;
D O I
10.1055/s-2003-41462
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A convergent and enantioselective synthesis of the C3-C19 bis-oxane oxazole fragment of phorboxazole B has been described. This work features highly efficient substrate-controlled reductions to construct the functionalised cis-oxane and a Mukaiyama aldol reaction followed by an intramolecular Williamson reaction leading to a trans-oxane.
引用
收藏
页码:1817 / 1821
页数:5
相关论文
共 50 条
  • [31] Studies on the synthesis of reidispongiolide A: stereoselective synthesis of the C(22)-C(36) fragment
    Ying, Maben
    Roush, William R.
    TETRAHEDRON, 2011, 67 (52) : 10274 - 10280
  • [32] Synthetic studies on mycalolide B: Synthesis of the C7-C35 fragment
    Kimura, Tomoyuki
    Kuribayashi, Satomi
    Sengoku, Tetsuya
    Matsui, Keita
    Ueda, Shoko
    Hayakawa, Ichiro
    Suenaga, Kiyotake
    Kigoshi, Hideo
    CHEMISTRY LETTERS, 2007, 36 (12) : 1490 - 1491
  • [33] Synthetic studies towards the total synthesis of tedanolide: formation of the C(13)-C(23) fragment
    Loh, TP
    Feng, LC
    TETRAHEDRON LETTERS, 2001, 42 (18) : 3223 - 3226
  • [34] Stereoselective synthesis of Hantupeptins A, B and C common fragment
    Srinivas, A.
    Sunitha, M.
    Rao, C. Govind
    INDIAN JOURNAL OF CHEMISTRY SECTION B-ORGANIC CHEMISTRY INCLUDING MEDICINAL CHEMISTRY, 2016, 55 (10): : 1239 - 1242
  • [35] Synthetic studies on bafilomycin A1:: stereoselective synthesis of the enantiopure C1-C11 fragment
    Quéron, E
    Lett, R
    TETRAHEDRON LETTERS, 2004, 45 (23) : 4527 - 4531
  • [36] Stereoselective synthesis of C19-C27 fragment of bryostatin 11
    Yadav, J. S.
    Swamy, T.
    Reddy, B. V. Subba
    Ravinder, V.
    TETRAHEDRON LETTERS, 2014, 55 (30) : 4054 - 4056
  • [37] Stereoselective synthesis of the C8-C19 lacton fragment of Carolacton
    Rasapalli, Sivappa
    Yu, Menglong
    Jarugumilli, Gopalakrishna
    Rao, Gangadhara
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2012, 244
  • [38] Studies on the total synthesis of sanglifehrin A: stereoselective synthesis of the C(29)-C(39) fragment
    Dias, LC
    Salles, AG
    TETRAHEDRON LETTERS, 2006, 47 (13) : 2213 - 2216
  • [39] SYNTHETIC STUDIES TOWARDS NOVEL TRIS-OXAZOLE BASED MACROLIDES OF MARINE ORIGIN - STEREOCONTROLLED SYNTHESIS OF THE C20-C35 FRAGMENT IN ULAPUALIDE-A
    CHATTOPADHYAY, SK
    PATTENDEN, G
    TETRAHEDRON LETTERS, 1995, 36 (29) : 5271 - 5274
  • [40] Studies on the total synthesis of amphidinolide O. A stereoselective synthesis of C3-C11 fragment
    Pang, JH
    Ham, YJ
    Lee, DH
    BULLETIN OF THE KOREAN CHEMICAL SOCIETY, 2003, 24 (07) : 891 - 892