Stereoselective Synthesis of the C25-C36 Segment of Arenicolides A and B: Determination of the Configuration of the Trisubstituted Epoxide

被引：5
作者：
Nagumo, Shinji [1 ]
Nakano, Taeko [1 ]
Hata, Kyomi [1 ]
Mizukami, Megumi [2 ]
Miyashita, Masaaki [1 ]
机构：
[1] Kogakuin Univ, Dept Appl Chem, Tokyo 1920015, Japan
[2] Hokkaido Pharmaceut Univ, Sch Pharm, Otaru, Hokkaido 0470264, Japan
来源：
ORGANIC LETTERS | 2010年 / 12卷 / 05期
关键词：
1,3-DIOL ACETONIDES; STEREOCHEMISTRY; CATALYST; ALCOHOLS; ACID;
D O I：
10.1021/ol902750e
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Two diastereomeric epoxides 4a and 4b corresponding to the C-25-C-36 fragment of arenicolides A and B were synthesized in a stereoselective manner involving the Pd(0)-catalyzed stereospecific methoxy substitution reaction of epoxy unsaturated ester 6 with B(OMe)(3) as the key step. Comparison of the H-1 NMR spectra of the synthetic compounds with that of arenicolide A revealed that the configuration of the epoxide in arenicolides A and B is 30R and 31R.
引用
收藏
页码：908 / 911
页数：4
相关论文
共 24 条
  • [1] Synthetic study of arenicolide C: stereoselective synthesis of the C19-C36 segment
    Sunagawa, Sho
    Yamada, Haruki
    Naito, Minako
    Yasui, Eiko
    Mizukami, Megumi
    Miyashita, Masaaki
    Nagumo, Shinji
    TETRAHEDRON LETTERS, 2015, 56 (48) : 6693 - 6695
  • [2] Stereoselective synthesis of the C1-C20 segment of the microsclerodermins A and B
    Chandrasekhar, S.
    Sultana, S. Shameem
    TETRAHEDRON LETTERS, 2006, 47 (40) : 7255 - 7258
  • [3] Towards the Synthesis of Lyngbyaloside B: Stereoselective Synthesis of the C1-C16 Macrolactone Core Segment
    Yadav, Jhillu S.
    Haldar, Animesh
    Maity, Tapas
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2013, 2013 (15) : 3076 - 3085
  • [4] Stereoselective synthesis and absolute configuration of the C33-C42 fragment of symbiodinolide
    Takamura, Hiroyoshi
    Kadonaga, Yuichiro
    Yamano, Yoshi
    Han, Chunguang
    Kadota, Isao
    Uemura, Daisuke
    TETRAHEDRON, 2009, 65 (36) : 7449 - 7456
  • [5] 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
  • [6] Synthetic studies on cytotoxic macrolides cruentarens A and B: stereoselective synthesis of the C8-C19 segment of cruentarens A and B
    Prasad, Busam Ramalinga Vara
    Meshram, Harshadas Mitaram
    TETRAHEDRON-ASYMMETRY, 2010, 21 (15) : 1837 - 1844
  • [7] Synthetic studies of venturicidins: stereoselective synthesis of the C15-C27 segment based on two types of stereospecific epoxide opening reactions
    Suzuki, Yuji
    Nagumo, Shinji
    Yasui, Eiko
    Mizukami, Megumi
    Miyashita, Masaaki
    TETRAHEDRON LETTERS, 2011, 52 (51) : 6948 - 6951
  • [8] Concise epoxide-based synthesis of the C14-C25 bafilomycin A1 polypropionate chain
    Valentin, Elizabeth M.
    Mulero, Marlenne
    Prieto, Jose A.
    TETRAHEDRON LETTERS, 2012, 53 (17) : 2199 - 2201
  • [9] Stereoselective Total Synthesis of (-)-Isocladospolide B and Cladospolide B and C
    Yadav, J. S.
    Mandal, S. S.
    SYNLETT, 2011, (19) : 2803 - 2806
  • [10] First stereoselective total synthesis of ophiocerins B and c
    Yadav, J. S.
    Lakshmi, P. Naga
    Harshavardhan, S. J.
    Reddy, B. V. Subba
    SYNLETT, 2007, (12) : 1945 - 1947
123