Yamaguchi Esterification

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Palakodety Radha Krishna - One of the best experts on this subject based on the ideXlab platform.

Debendra K. Mohapatra - One of the best experts on this subject based on the ideXlab platform.

Jhillu S. Yadav - One of the best experts on this subject based on the ideXlab platform.

Krishna P. Kaliappan - One of the best experts on this subject based on the ideXlab platform.

  • Synthetic studies on palmerolide C: synthesis of an advanced intermediate towards the revised structure of palmerolide C
    Organic & biomolecular chemistry, 2020
    Co-Authors: Ashik A. Sayyad, Khushboo Kaim, Krishna P. Kaliappan
    Abstract:

    A stereoselective synthesis of the highly advanced intermediates towards the revised structure of palmerolide C and 10-epi-palmerolide C is described in this paper. The required key fragments C1-C6, C7-C14 and C15-C23 have been successfully assembled in a convergent manner to access the C1-C23 framework bearing all the five stereocenters present in the natural product. The synthesis involves the Julia-Kocienski reaction, Yamaguchi Esterification, Takai olefination and regioselective epoxide opening as key steps. The proposed route is flexible and could also be applied to the synthesis of structurally related palmerolides.

  • A Shimizu Non‐Aldol Approach to the Formal Total Synthesis of Palmerolide A
    Chemistry an Asian journal, 2011
    Co-Authors: Sandip A. Pujari, Parthasarathy Gowrisankar, Krishna P. Kaliappan
    Abstract:

    A formal total synthesis of palmerolide A has been accomplished by assembling three fragments by means of successive Julia-Kocienski olefination, Yamaguchi Esterification, and ring-closing metathesis (RCM). Our initial efforts to combine the first two fragments through a Julia-Kocienski reaction between a secondary sulfone and a ketone were not successful; nevertheless, it was feasible between a primary sulfone and aldehyde. Yamaguchi Esterification with the third fragment then set the stage for a RCM reaction. Initial failure of the RCM with a PMB-ether adjacent to the olefins and the difficulty in cleaving the PMB-ether prompted us to change the choice of protecting groups, which then paved the way to the macrocyclic core of palmerolide A.

Biswanath Das - One of the best experts on this subject based on the ideXlab platform.