First asymmetric total synthesis of aspergillide D

被引：10
|
作者：
Jena, Bighnanshu K. [1 ]
Reddy, G. Sudhakar [1 ]
Mohapatra, Debendra K. [1 ]
机构：
[1] CSIR Indian Inst Chem Technol, Nat Prod Chem Div, Hyderabad 500007, Andhra Pradesh, India
来源：
ORGANIC & BIOMOLECULAR CHEMISTRY | 2017年 / 15卷 / 08期
关键词：
CARBODIIMIDE CHEMISTRY; SECONDARY ALCOHOLS; MIXED ANHYDRIDE; MARINE ISOLATE; MACROLIDE; FUNGUS; ACIDS; ESTERIFICATION; DEPROTECTION; SELECTIVITY;
D O I：
10.1039/c6ob02435a
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The first asymmetric total synthesis of a 16-membered macrolide, aspergillide D, is described. The chiral centers of the acid are derived from D-ribose and the alcohol subunit from 1,8-octane diol through Sharpless kinetic resolution, respectively. The other key reactions include Yamaguchi esterification, ring-closing metathesis reaction, and Shiina macrolactonization to construct the fully functionalized macrocycle.
引用
收藏
页码：1863 / 1871
页数：9
相关论文
共 50 条
  • [31] Synthesis of aspergillide A from a synthetic intermediate of aspergillide B
    Nagasawa, Tomohiro
    Kuwahara, Shigefumi
    TETRAHEDRON LETTERS, 2010, 51 (05) : 875 - 877
  • [32] Stereodivergent Total Synthesis of (+)-Aspergillide B and (+)-7-epi-Aspergillide A (vol 2013, pg 578, 2013)
    Sridhar, Y.
    Srihari, P.
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2014, 2014 (07) : 1557 - 1557
  • [33] Total asymmetric synthesis of sperabillins B and D
    Davies, SG
    Kelly, RJ
    Mortimer, AJP
    CHEMICAL COMMUNICATIONS, 2003, (17) : 2132 - 2133
  • [34] First Asymmetric Total Synthesis and Insight into the Structure of Laurenidificin
    Yoshikawa, Yusuke
    Yamakawa, Maki
    Kobayashi, Tetsuya
    Murai, Kenichi
    Arisawa, Mitsuhiro
    Sumimoto, Michinori
    Fujioka, Hiromichi
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2017, 2017 (19) : 2715 - 2718
  • [35] The first asymmetric total synthesis of lycoposerramine-R
    Ishida, Hiroaki
    Kimura, Shinya
    Kogure, Noriyuki
    Kitajima, Mariko
    Takayama, Hiromitsu
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2015, 13 (28) : 7762 - 7771
  • [36] First asymmetric total synthesis of Mansonone P and R
    Peng, XJ
    She, XG
    Wang, ZK
    Quan, WG
    Pan, XF
    JOURNAL OF THE CHINESE CHEMICAL SOCIETY, 2004, 51 (06) : 1367 - 1371
  • [37] First asymmetric total synthesis of (-)-(R)- and (+)-(S)-geibalansine
    Morel, AF
    Larghi, EL
    TETRAHEDRON-ASYMMETRY, 2004, 15 (01) : 9 - 10
  • [38] The first total synthesis of (±)-colabomycin D
    Wei, XD
    Grové, JJC
    Taylor, RJK
    JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1999, (09): : 1143 - 1145
  • [39] The first total synthesis of dragmacidin D
    Garg, NK
    Sarpong, R
    Stoltz, BM
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (44) : 13179 - 13184
  • [40] First total synthesis of (+)-koninginin D
    Liu, G
    Wang, ZQ
    CHEMICAL COMMUNICATIONS, 1999, (12) : 1129 - 1130
12345