Synthesis 2012; 44(11): 1663-1666
DOI: 10.1055/s-0031-1290986
paper
© Georg Thieme Verlag Stuttgart · New York

Protecting Group-Free Syntheses of (4S,5S,11R)- and (4S,5S,11S)-iso-Cladospolide B and Their Biological Evaluation

Authors

  • Chada Raji Reddy*

    a   Division of Natural Products Chemistry, CSIR-Indian Institute of Chemical Technology, Hyderabad 500007, India
  • Nagavaram Narsimha Rao

    a   Division of Natural Products Chemistry, CSIR-Indian Institute of Chemical Technology, Hyderabad 500007, India
  • Pombala Sujitha

    b   Chemical Biology Laboratory, CSIR-Indian Institute of Chemical Technology, Hyderabad 500007, India, Fax: +91(40)27160512   Email: rajireddy@iict.res.in
  • Chityal Ganesh Kumar

    b   Chemical Biology Laboratory, CSIR-Indian Institute of Chemical Technology, Hyderabad 500007, India, Fax: +91(40)27160512   Email: rajireddy@iict.res.in
Further Information

Publication History

Received: 20 February 2012

Accepted after revision: 03 April 2012

Publication Date:
09 May 2012 (online)


Graphical Abstract

Abstract

Short and efficient total syntheses of (4S,5S,11R)- and (4S,5S,11S)-iso-cladospolide B were achieved in five steps each without using any protecting groups. The key steps were an alkyne-zipper reaction, a Suzuki cross coupling, and a Sharpless asymmetric dihydroxylation. The biological activities of both natural products toward various cancer cell lines were tested for the first time.