Synlett 2023; 34(06): 673-677
DOI: 10.1055/a-1881-0529
cluster
Chemical Synthesis and Catalysis in India

Synthesis of the Key Skeleton of Phosphoeleganin

Gour Hari Mandal
,
Dhiman Saha
,
Sourya Shankar Auddy
,
Financial support from the Science and Engineering Research Board, India (Project no. CRG/2019/001664), for carrying out this work is gratefully acknowledged.


Abstract

The asymmetric synthesis of the key skeleton of phosphoeleganin has been achieved for the first time by using a convergent approach. The salient features of this synthesis include amidation to install a glycine amide at the C-1 position, Wittig olefination to access the C5–C6 bond, Julia–Kocienski olefinations to prepare the C9–C10 and C13–C14 bonds, and a Takai olefination and a Sonogashira coupling to construct the C17–C18 and C18–C19 bonds, respectively. The route disclosed is highly modular, which will permit the synthesis of various analogues, useful for structure–activity relationship studies on phosphoeleganins.

Supporting Information



Publikationsverlauf

Eingereicht: 13. Mai 2022

Angenommen nach Revision: 21. Juni 2022

Accepted Manuscript online:
21. Juni 2022

Artikel online veröffentlicht:
19. Juli 2022

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