Development of a Stereospecific Strategy for the Total Synthesis of Diplodialide C and Formal Synthesis of (-)-Curvularin

被引:0
|
作者
Kumar, Ravan [1 ]
Banerjee, Amit [1 ]
Saha, Sumit [1 ]
机构
[1] Natl Inst Technol Sikkim, Dept Chem, Ravangla 737139, India
关键词
total synthesis; natural products; pentaketides; macrolide; epoxides; Shiina macrolactonization; STEREOSELECTIVE-SYNTHESIS;
D O I
10.1055/s-0043-1775057
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A concise and efficient stereospecific approach for the total synthesis of diplodialide C (R, R and S, S isomers) has been demonstrated using chiral homoglycidol and propylene oxide as a source of starting material. Further oxidized ketolide product derived from diplodialide C (S, S isomer) was applied to the formal synthesis of (-)-curvularin following reported known literature.
引用
收藏
页码:679 / 682
页数:4
相关论文
共 50 条
  • [1] A concise stereoselective total synthesis of diplodialide C
    Bommareddy Pratapareddy
    Reddymasu Sreenivasulu
    Islavathu Hatti
    Mandava Venkata Basaveswara Rao
    Rudraraju Ramesh Raju
    Monatshefte für Chemie - Chemical Monthly, 2015, 146 : 1921 - 1926
  • [2] A concise stereoselective total synthesis of diplodialide C
    Pratapareddy, Bommareddy
    Sreenivasulu, Reddymasu
    Hatti, Islavathu
    Rao, Mandava Venkata Basaveswara
    Raju, Rudraraju Ramesh
    MONATSHEFTE FUR CHEMIE, 2015, 146 (11): : 1921 - 1926
  • [3] Total synthesis of (-)-curvulain and formal total synthesis of (+)-12-oxo-curvularin and (-)-citreofuran
    Jennings, Michael P.
    De Joarder, Dripta
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2014, 247
  • [4] TOTAL SYNTHESIS OF (+/-)-DIPLODIALIDE-A
    ISHIDA, T
    WADA, K
    JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1979, (02): : 323 - 327
  • [5] Stereoselective total synthesis of diplodialide A
    Kolluri Ramakrishna
    Reddymasu Sreenivasulu
    Mandava Venkata Basaveswara Rao
    Siddaiah Vidavalur
    Boggu Jagan Mohan Reddy
    Chemical Papers, 2021, 75 : 931 - 937
  • [6] TOTAL SYNTHESIS OF (+/-)-DIPLODIALIDE-A
    ISHIDA, T
    WADA, K
    JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1977, (10) : 337 - 338
  • [7] Stereoselective total synthesis of diplodialide A
    Ramakrishna, Kolluri
    Sreenivasulu, Reddymasu
    Rao, Mandava Venkata Basaveswara
    Vidavalur, Siddaiah
    Reddy, Boggu Jagan Mohan
    CHEMICAL PAPERS, 2021, 75 (03): : 931 - 937
  • [8] TOTAL SYNTHESIS OF A CURVULARIN ISOMER
    BAGLI, JF
    IMMER, H
    CANADIAN JOURNAL OF CHEMISTRY, 1968, 46 (19): : 3115 - &
  • [9] Stereospecific formal total synthesis of ecteinascidin 743
    Zheng, SP
    Chan, C
    Furuuchi, T
    Wright, BJD
    Zhou, B
    Guo, J
    Danishefsky, S
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2006, 45 (11) : 1754 - 1759
  • [10] Stereoselective total synthesis of (-)-curvularin
    Radha Krishna, Muniganti
    Sridhar, Gattu
    Syed, Tasqeeruddin
    Jayaprakash, H. V.
    SYNTHETIC COMMUNICATIONS, 2022, 52 (01) : 37 - 42