Concepedia

The First Total Synthesis of (−) and (+)-2-Hydroxy-24-oxooctacosanolide Using an Effective Lactonization

Isamu Shiina, Takaaki Kikuchi, Akane Sasaki

Organic Letters · 2006 · 35 citations · 15 references

DOI

Concepts

Abstract

[structure: see text] An effective method for the total synthesis of 2-hydroxy-24-oxooctacosanolide, a defensive salivary secretion of the African termite Pseudacanthotermes spiniger, has been developed. The key lactonization to form a 29-membered ring lactone core is performed using 2-methyl-6-nitrobenzoic anhydride with a catalytic amount of 4-(dimethylamino)pyridine N-oxide.

References

15

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Enantioselective Total Synthesis of Octalactin A Using Asymmetric Aldol Reactions and a Rapid Lactonization To Form a Medium‐Sized Ring

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