Stereoselective total synthesis of (-)-(5S,8R,13S,16R)-pyrenophorol

被引:12
|
作者
Edukondalu, Perugu [1 ]
Sreenivasulu, Reddymasu [1 ]
Chiranjeevi, Barreddi [2 ]
Kumar, Vuppula Naresh [3 ]
Raju, Rudraraju Ramesh [1 ]
机构
[1] Acharya Nagarjuna Univ, Dept Chem, Nagarjuna Nagar 522510, Andhra Pradesh, India
[2] Indian Inst Chem Technol, Inorgan & Phys Chem Div, Hyderabad 500007, Andhra Pradesh, India
[3] Sri Chaitanya PG Coll, Dept Chem, Godavarikhani 505209, India
来源
MONATSHEFTE FUR CHEMIE | 2015年 / 146卷 / 08期
关键词
(S)-Propylene epoxide; Cross-metathesis reaction; Intermolecular Mitsunobu cyclization; (-)-Pyrenophorol; MACRODIOLIDE PYRENOPHOROL; COLLETOTRICHUM-CAPSICI; SECONDARY METABOLITES; KINETIC RESOLUTION; TERMINAL EPOXIDES; (-)-PYRENOPHOROL; COLLETODIOL; DILACTONE; PRODUCTS;
D O I
10.1007/s00706-014-1406-3
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The total synthesis of 16-membered C (2)-symmetric dilactone (-)-(5S,8R,13S,16R)-pyrenophorol was accomplished starting from enantiomerically pure propylene oxide prepared by hydrolytic kinetic resolution of (+/-)-propylene oxide with key steps of cross-metathesis and intermolecular Mitsunobu cyclization for the construction of macrolactone.
引用
收藏
页码:1309 / 1314
页数:6
相关论文
共 50 条
  • [41] Synthesis of murisolin, (15R, 16R, 19R, 20S)-murisolin A, and (15R, 16R, 19S, 20S)-16,19-cis-murisolin and their inhibitory action with bovine heart mitochondrial complex I
    Hattori, Yasunao
    Kimura, Yuka
    Moroda, Aki
    Konno, Hiroyuki
    Abe, Masato
    Miyoshi, Hideto
    Goto, Tetsuhisa
    Makabe, Hidefumi
    CHEMISTRY-AN ASIAN JOURNAL, 2006, 1 (06) : 894 - 904
  • [42] Synthesis of (4R,8R)- and (4S,8R)-4,8-dimethyldecanal:: the common aggregation pheromone of flour beetles
    Santangelo, Ellen M.
    Correa, Arlene G.
    Zarbin, Paulo H. G.
    TETRAHEDRON LETTERS, 2006, 47 (29) : 5135 - 5137
  • [43] Asymmetric synthesis of (-)-nupharamine and (-)-(5S, 8R, 9S)-5-(3-furyl)-8-methyloctahydroindolizidine from β-amino ketones and the intramolecular Mannich reaction
    Davis, Franklin A.
    Santhanaraman, Manikandan
    JOURNAL OF ORGANIC CHEMISTRY, 2006, 71 (11): : 4222 - 4226
  • [44] THE TOTAL SYNTHESIS OF OPTICALLY PURE (9R,13S)-7-DEOXY-13-DIHYDRODAUNOMYCINONE AND (9R,13R)-7-DEOXY-13-DIHYDRODAUNOMYCINONE
    RUSSELL, RA
    IRVINE, RW
    WARRENER, RN
    JOURNAL OF ORGANIC CHEMISTRY, 1986, 51 (09): : 1595 - 1599
  • [45] TOTAL SYNTHESIS OF 11(R,S)-HETE (13)
    JUST, G
    LUTHE, C
    TETRAHEDRON LETTERS, 1982, 23 (13) : 1331 - 1334
  • [46] Synthesis of (-)-(1S,5R)- and (+)-(1R,5S)-trifluoroanalogues of frontalin
    Bravo, P
    Corradi, E
    Frigerio, M
    Meille, SV
    Panzeri, W
    Pesenti, C
    Viani, F
    TETRAHEDRON LETTERS, 1999, 40 (34) : 6317 - 6320
  • [47] Total synthesis of (4R,5S)-melithiazol C and (3R,4S)-cystothiazole E
    Takayama, Hiroyuki
    Kato, Keisuke
    Kimura, Masayuki
    Akita, Hiroyuki
    HETEROCYCLES, 2007, 71 (01) : 75 - 85
  • [48] Total synthesis of 5(R)- and 5(S)-polyandrane
    Walker, DP
    Grieco, PA
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (42) : 9891 - 9892
  • [49] Total synthesis of (-)-(8R, 10S)- and (+)-(8S, 10R)-8-hydroxypolypoda-13,17,21-triene based on enzymatic resolution
    Kinoshita, M
    Nakamura, D
    Fujiwara, N
    Akita, H
    JOURNAL OF MOLECULAR CATALYSIS B-ENZYMATIC, 2003, 22 (3-4) : 161 - 172
  • [50] Stereoselective approaches for the total synthesis of polyacetylenic (3R,8S)-falcarindiol
    Sabitha, Gowravaram
    Bhaskar, Vangala
    Reddy, Ch. Srinivas
    Yadav, Jhillu S.
    SYNTHESIS-STUTTGART, 2008, (01): : 115 - 121