1315552-07-8

Usage

Uses

Used in Pharmaceutical Industry:
N-Boc-norloline is used as an intermediate in the synthesis of Loline (I707255) for its potential applications in the development of new pharmaceutical compounds. The alkaloid Loline, isolated from fungal endophytes, has shown promising properties that can be harnessed for therapeutic purposes.
Used in Chemical Research:
N-Boc-norloline is also used as a research compound in the field of organic chemistry. Its unique structure and reactivity make it a valuable tool for understanding various chemical reactions and mechanisms, which can lead to the discovery of new synthetic pathways and the development of novel compounds with potential applications in various industries.

Upstream product

• 1315552-05-6 C₇H₁₁ClN₄O 
• 24424-99-5 di-tert-butyl dicarbonate 
• 1315552-06-7 C₇H₁₀N₄O 

Downstream Products

• 25161-91-5 (+)-Loline 
• 38964-33-9 N-formylloline 
• 25161-92-6 (+)-Loline dihydrochloride 

Relevant academic research and scientific papers

Stereoselective synthesis of (+)-loline alkaloid skeleton

The loline alkaloids present a compact polycyclic pyrrolizidine skeleton and contain a strained five-membered ethereal bridge, structural features that have proven challenging for synthetic chemists to incorporate since the discovery of this natural product family more than 100 years ago. These alkaloids are produced by mutualistic fungal symbionts (endophytes) living on certain species of pasture grasses and protect the host plant from insect herbivory. The asymmetric total synthesis of loline alkaloids is reported and extends our first-generation (racemic) synthesis of this alkaloid family. Key to the synthesis is a diastereoselective tethered aminohydroxylation of a homoallylic carbamate function and a Petasis Borono-Mannich addition.

An efficient synthesis of loline alkaloids

Loline (1) is a small alkaloid that, in spite of its simple-looking structure, has posed surprising challenges to synthetic chemists. It has been known for more than a century and has been the subject of extensive biological investigations, but only two total syntheses have been achieved to date. Here, we report an asymmetric total synthesis of loline that, with less then ten steps, is remarkably short. Our synthesis incorporates a Sharpless epoxidation, a Grubbs olefin metathesis and an unprecedented transannular aminobromination, which converts an eight-membered cyclic carbamate into a bromopyrrolizidine. The synthesis is marked by a high degree of chemo- and stereoselectivity and gives access to several members of the loline alkaloid family. It delivers sufficient material to support a programme aimed at studying the complex interactions between plants, fungi, insects and bacteria brokered by loline alkaloids.