The First Total Synthesis of Pectinolides D and E and Total Synthesis of Pectinolides A and C

被引:5
|
作者
Sabitha, Gowravaram [1 ]
AnkiReddy, Praveen [1 ]
Das, Sukant Kishore [1 ]
机构
[1] Indian Inst Chem Technol, CSIR, Nat Prod Chem Div, Hyderabad 500007, Andhra Pradesh, India
来源
SYNTHESIS-STUTTGART | 2015年 / 47卷 / 03期
关键词
pectinolides; first synthesis; aldehyde-alkyne coupling; Noyori reduction; Still-Genari cis-olefination; STEREOSELECTIVE TOTAL-SYNTHESIS; HYPTIS-PECTINATA; D-MANNITOL; LACTONE;
D O I
10.1055/s-0034-1378912
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The first total synthesis of pectinolides D and E and total synthesis of pectinolides A and C was achieved from a hitherto unknown common key building block prepared from readily available D-mannitol. Key reactions involved in the synthesis are Red-Al reduction of an epoxy alcohol, enantioselective Noyori reduction of ynones, aldehyde-alkyne coupling, and Still-Genari cis-olefination.
引用
收藏
页码:330 / 342
页数:13
相关论文
共 50 条
  • [1] Stereoselective Total Synthesis of Pectinolides A, C, and H
    Ghogare, Ramesh Saudagar
    Wadavrao, Sachin Bibishan
    Narsaiah, Akkirala Venkat
    HELVETICA CHIMICA ACTA, 2016, 99 (04) : 247 - 254
  • [2] The stereoselective total syntheses of pectinolides A, B, and C
    Ramulu, Udugu
    Ramesh, Dasari
    Reddy, Sudina Purushotham
    Rajaram, Singanaboina
    Babu, Katragadda Suresh
    TETRAHEDRON-ASYMMETRY, 2014, 25 (20-21) : 1409 - 1417
  • [3] First total synthesis of sterenins A, C and D
    Shinozuka, Tsuyoshi
    Yamamoto, Yuko
    Hasegawa, Toru
    Salto, Keiji
    Naito, Satoru
    TETRAHEDRON LETTERS, 2008, 49 (10) : 1619 - 1622
  • [4] First total synthesis of carbazomycin C and D
    Knolker, HJ
    Schlechtingen, G
    JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1997, (04): : 349 - 350
  • [5] Total Synthesis of Myceliothermophins C, D, and E
    Nicolaou, K. C.
    Shi, Lei
    Lu, Min
    Pattanayak, Manas R.
    Shah, Akshay A.
    Ioannidou, Heraklidia A.
    Lamani, Manjunath
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2014, 53 (41) : 10970 - 10974
  • [6] First Total Synthesis of Artekeiskeanol A, C and Altissimacoumarin D
    Talakokkula, Anil
    Baikadi, Karunakar
    Narsaiah, A. Venkat
    SYNOPEN, 2019, 3 (02): : 49 - 54
  • [7] First stereoselective total synthesis of pectinolide C and total synthesis of pectinolide A
    Sabitha, Gowravaram
    Das, Sukant Kishore
    AnkiReddy, Praveen
    Yadav, J. S.
    TETRAHEDRON LETTERS, 2013, 54 (09) : 1097 - 1099
  • [8] The first stereoselective and the total synthesis of Leiocarpin C and total synthesis of (+)-Goniodiol
    Yadav, J. S.
    Premalatha, K.
    Harshavardhan, S. J.
    Reddy, B. V. Subba
    TETRAHEDRON LETTERS, 2008, 49 (48) : 6765 - 6767
  • [9] First total synthesis of (+)-heteroplexisolide E
    Kutsumura, Noriki
    Kiriseko, Akito
    Saito, Takao
    TETRAHEDRON LETTERS, 2012, 53 (26) : 3274 - 3276
  • [10] The first total synthesis of (-)-bitungolide E
    Shashidhar, J.
    Reddy, K. Mahender
    Ghosh, Subhash
    TETRAHEDRON LETTERS, 2011, 52 (24) : 3106 - 3109