642486-88-2

Upstream product

• 335163-22-9 (1'R,3R,5S)-3-hydroxy-5-(1'-methylbut-3'-enyl)dihydrofuran-2-one 
• 325172-28-9 2-allyl-6-methoxy-benzoic acid 
• 579-75-9 2-Methoxybenzoic acid 
• 335163-24-1 Trifluoro-methanesulfonic acid (R)-1-((3aR,5S,6aR)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-ethyl ester 
• 335163-25-2 (1'R,2R,3R,5S)-2,2-dimethyl-5-(1'-methylbut-3'-enyl)tetrahydrofuro[2,3-d][1,3]dioxole 
• 335163-26-3 (1'R,3R,5S)-5-(1'-methylbut-3'-enyl)tetrahydrofuran-2,3-diol 
• 58475-17-5 (R)-1-((3aR,5S,6aR)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl)ethan-1-ol 

Relevant academic research and scientific papers

Formal Total Synthesis of (+)-Salicylihalamides A and B: A Combined Chiral Pool and RCM Strategy

The formal total synthesis of the (+)-salicylihalamides A and B is detailed, utilizing a chiral pool approach to generate the three stereogenic centers and a ring-closing metathesis (RCM) for the formation of the macrocyclic ring structure. Starting from a known glucose-derived alcohol, the formal total synthesis was achieved in an efficient 13-step protocol in 26% overall yield. It was found that substitution at the remote phenolic group significantly influenced the ratio of the E-and Z-double bond products in the RCM step. The introduction of phenol protecting groups provided E-isomers preferentially and also enhanced the rates of the RCM reactions.