1204754-01-7

Upstream product

• 1446246-63-4 (4S)-2-(4-methoxyphenyl)-4-propyl-1,3-dioxane 

Downstream Products

• 1204754-02-8 C₁₄H₂₀O₃ 
• 1446246-67-8 (E)-4-((4R,5R)-5-((S)-2-(4-methoxybenzyloxy)pentyl)-2,2-dimethyl-1,3-dioxolan-4-yl)but-3-en-2-one 
• 1446246-66-7 {(4R,5R)-5-((S)-2-(4-methoxybenzyloxy)pentyl)-2,2-dimethyl-1,3-dioxolan-4-yl}methyl benzoate 
• 1446246-65-6 (2R,3R,5S)-2,3-dihydroxy-5-(4-methoxybenzyloxy)octyl benzoate 
• 1446246-64-5 (S,E)-5-(4-methoxybenzyloxy)oct-2-en-1-ol 
• 1446273-06-8 ethyl (S,E)-5-(4-methoxybenzyloxy)oct-2-enoate 
• 1446246-62-3 (S,E)-5-(4-methoxybenzyloxy)oct-2-enylbenzoate 
• 1446246-61-2 ((4R,5R)-5-((S)-2-(4-methoxybenzyloxy)pentyl)-2,2-dimethyl-1,3-dioxolan-4-yl)methanol 

Relevant academic research and scientific papers

First stereoselective total synthesis of phomonol via oxa-Michael approach

Herein we report the first stereoselective total synthesis of phomonol via Sharpless asymmetric dihydroxylation and 6-exo-trig oxa-Michael addition as the key steps.

Total synthesis and biological evaluation of (+)-neopeltolide and its analogues

The stereocontrolled total synthesis of the originally proposed (1) and correct (2) structures of (+)-neopeltolide, a novel marine macrolide natural product with highly potent antiproliferative activity against several cancer cell lines as well as potent antifungal activity, has been achieved by exploiting a newly developed SuzukiMiyaura coupling/ring-closing metathesis strategy. Alkylborate 44, which was generated in situ from iodide 34, was coupled with enol phosphate 8 by a Suzuki-Miyaura coupling. Ring-closing metathesis of the derived diene 45 followed by stereoselective hydrogenation afforded tetrahydropyran 47 as a single stereoisomer in high overall yield from 34. Our convergent strategy enabled us to construct the 14-membered macrolactone core structure of 2 in a rapid and efficient manner. Total synthesis and biological evaluation of synthetic intermediates and designed synthetic analogues, performed to establish the structure-activity relationships of 2, led to the discovery of a structurally simple yet potent cytotoxic analogue, 9-demethylneopeltolide (54).