760181-73-5

Upstream product

• 925-90-6 ethylmagnesium bromide 
• 874660-40-9 (R)-2-(4-Methoxy-benzyloxy)-pent-4-enal 
• 289619-05-2 (S)-4-Benzyl-3-[(R)-2-(4-methoxy-benzyloxy)-pent-4-enoyl]-oxazolidin-2-one 
• 1779-49-3 Methyltriphenylphosphonium bromide 
• 760181-72-4 (R)-2-(4-methoxybenzyloxy)pent-4-en-1-ol 

Downstream Products

• 760181-76-8 Chloro-acetic acid (S)-2,4-bis-benzyloxy-1-((1R,2R)-1-ethyl-2-triisopropylsilanyloxy-pent-4-enyloxy)-butyl ester 
• 760181-77-9 ((R)-1-{(R)-1-[(R)-1-((S)-1,3-Bis-benzyloxy-propyl)-but-3-enyloxy]-propyl}-but-3-enyloxy)-triisopropyl-silane 
• 760181-75-7 (S)-2,4-Bis-benzyloxy-butyric acid (1R,2R)-1-ethyl-2-triisopropylsilanyloxy-pent-4-enyl ester 
• 760181-80-4 (S)-2,4-Bis-benzyloxy-butyric acid (1R,2R)-1-ethyl-2-hydroxy-pent-4-enyl ester 
• 760181-74-6 (S)-2,4-Bis-benzyloxy-butyric acid (1R,2R)-1-ethyl-2-(4-methoxy-benzyloxy)-pent-4-enyl ester 

Relevant academic research and scientific papers

An approach to lauroxanes by iterative use of Co2(CO) 6-acetylenic complexes. A formal synthesis of (+)-laurencin

A new approach to lauroxanes by a powerful and highly convergent methodology based on iterative use of Co2(CO)6-acetylenic complexes is described. The strategy employs an intermolecular Nicholas reaction to form unsaturated branched linear ethers, a ring closing metathesis to obtain the cobalt complex cyclic ethers, and an isomerization promoted by montmorillonite K-10. A short synthesis of cyclic ethers of seven-, eight-, and nine-membered rings is described. Additionally, the methodology is exemplified by the formal synthesis of (+)-laurencin, a red algae metabolite.

A new approach to the synthesis of cyclic ethers via the intermolecular allylation of α-acetoxy ethers and ring-closing metathesis

A concise synthesis of the isolaurepinnacin skeleton 6 was achieved via the intermolecular allylation of the α-acetoxy ether 3 followed by ring-closing metathesis. This methodology was successfully applied to the convergent synthesis of the oxocene 15, an advanced synthetic intermediate for the total synthesis of laurencin.