209119-65-3

Upstream product

• 209119-61-9 Benzoic acid (1R,3S)-1-chloromethyl-3-hydroxy-5-methylene-non-8-enyl ester 
• 209119-59-5 Benzoic acid (1R,3R)-4-chloro-1-chloromethyl-3-hydroxy-butyl ester 
• 209119-60-8 Benzoic acid (R)-1-chloromethyl-2-(R)-oxiranyl-ethyl ester 
• 209119-58-4 (4R,6R)-4,6-Bis-chloromethyl-[1,3]dioxan-2-one 
• 209119-62-0 Benzoic acid (1R,3R)-1-chloromethyl-3-hydroxy-7-methoxycarbonyl-5-oxo-heptyl ester 

Relevant academic research and scientific papers

Synthesis of a key building block for a butyrolactone → 1,3-diol approach to the polyol part of roflamycoin

For preparing tris(γ-lactone) 3 the mono(γ-lactone) 6 was synthesized from the dichlorodiol 12 (99.8% ee). Bisepoxide 9 - derived from dichlorodiol 12 (99.8% ee) - was ring-opened with the Gilman cuprate from 2-lithio-1,5-hexadiene and Cul giving almost exclusively the monoepoxide 21; in five more steps, γ-lactone 30 with the same stereotriad as the target molecule 6 but a different protecting group was obtained. Monoepoxide 33 - also derived from dichlorodiol 12 - was ring-opened with the same Gilman cuprate affording compound 35. It was transformed into the correctly protected γ-lactone 6 in seven steps, key reactions being the ozonolysis 35 → 36 and the diastereoselective reduction 36 → anti-37.