Conjugate reduction of vinyl bisphosphonates

Harmon, Nyema M.; Gehrke, Nathaniel R.; Wiemer, David F.

doi:10.1016/j.tetlet.2022.154078

Cited by 1 publication

(1 citation statement)

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“…Coupled with the fact that ricinoleic acid, the primary fatty acid found in castor oil, is a naturally occurring HFA used in a variety of applications including medicinal purposes, we were interested in synthesizing a family of castor‐based bisphosphonates and thus set out to produce the unsaturated and saturated bisphosphonates 15a and 15b . Though a variety of methods of bisphosphonate synthesis can be found in the literature (Du et al, 2002; Harmon et al, 2022), the primary method of bisphosphonate synthesis is through alkylation of a methylene diphosphonate anion through an S N 2 process; this is the method we employed for the synthesis of castor‐based bisphosphonates (Shull et al, 2006; Wiemer et al, 2008). To undergo alkylation, our first goal was to modify castor oil to an electrophile that could be used for alkylation of the bisphosphonate anion.…”

Section: Introductionmentioning

confidence: 99%

Novel bisphosphonates via castor oil

Fayer,

Rosen,

Cermak

et al. 2023

J Americ Oil Chem Soc

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Hydroxy fatty acids (HFAs) have long been a staple component of feedstock oils with uses ranging from motor oils to food to pharmaceuticals. Castor oil, which contains the HFA ricinoleic acid as its principal component, is the most widely used source of HFA in the world. In addition, bisphosphonates are a functional moiety that has been shown to display a variety of industrial applications, ranging from use in water softeners to osteoporosis drugs, primarily due to their affinity for the calcium ion. We have long been interested in the modification of ricinoleic acid from castor oil to phosphorus derivatives, including α‐hydroxy phosphonates and phosphonic acids, and have now accomplished the synthesis of a family of ricinoleic‐derived bisphosphonates: one that retains the cis alkene found in ricinoleic acid and one where the alkene has undergone hydrogenation. These compounds have been produced in high yields and high purity and the synthesis of these compounds is reported.

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