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      Permanent link:
      https://www.ias.ac.in/article/fulltext/jcsc/131/03/0025

    • Keywords

       

      Cytotoxic; Heck cyclization; natural products; ring closing metathesis; total synthesis.

    • Abstract

       

      In this article the formal total synthesis of mandelalide A has been described in details. The highly convergent and flexible strategy developed for mandelalide A involved the construction of key building blocks ent-9 and 7, and their assembly to the target compound. For the synthesis and coupling of these buildingblocks, the Brown’s crotylation, Sharpless asymmetric dihydroxylation followed by in situ Williamson type etherification, modified Prins cyclization, Masamune-Roush olefination and Heck cyclization were employed, the latter being crucial for the highly stereoselective formation of the macrocycle of mandelalide A. Initially,Julia Kocienski olefination, ring-closing metathesis reaction were investigated for the synthesis of the aglycone of the proposed structure of the mandelalide A, and found to be unsuccessful.

    • Author Affiliations

       

      V YAMINI1 K MAHENDER REDDY1 2 A SHIVA KRISHNA1 J K LAKSHMI3 SUBHASH GHOSH1

      1. Organic Synthesis and Process Chemistry Division, CSIR-Indian Institute of Chemical Technology, Hyderabad, Telangana 500 007, India
      2. Department of Chemistry and Chemical Biology, Harvard University, Cambridge, MA 02138, USA
      3. Centre for NMR and Structural Chemistry, CSIR-Indian Institute of Chemical Technology, Hyderabad, Telangana 500 007, India

    • Dates

       
      Published
      March 2019
      Manuscript received
      26 November 2018
      Manuscript revised
      24 January 2019
      Accepted
      5 February 2019

    • Supplementary Material

       

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