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

Chada Raji Reddy; Nagavaram Narsimha Rao; Pombala Sujitha; Chityal Ganesh Kumar

doi:10.1055/s-0031-1290986

Synthesis, Table of Contents

Synthesis 2012; 44(11): 1663-1666
DOI: 10.1055/s-0031-1290986

paper

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

Chada Raji Reddy*

^aDivision of Natural Products Chemistry, CSIR-Indian Institute of Chemical Technology, Hyderabad 500007, India

,

Nagavaram Narsimha Rao

^aDivision of Natural Products Chemistry, CSIR-Indian Institute of Chemical Technology, Hyderabad 500007, India

,

Pombala Sujitha

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

,

Chityal Ganesh Kumar

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

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Abstract

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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.

Key words

total synthesis - protecting groups - coupling - lactones

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References

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