274933-34-5

Upstream product

• 274933-33-4 2-[2-((S)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-acetylamino]-3-hydroxy-propionic acid methyl ester 
• 95422-24-5 methyl (3S)-3,4-O-isopropylidene-3,4-dihydroxybutanoate 
• 365217-57-8 (R)-2-[2-((S)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-acetylamino]-3-hydroxy-propionic acid methyl ester 
• 87319-12-8 (S)-2-(2,2-dimethyl-1,3-dioxolan-4-yl)acetic acid 
• 365217-72-7 2-((S)-2,2-Dimethyl-[1,3]dioxolan-4-ylmethyl)-4,5-dihydro-oxazole-4-carboxylic acid methyl ester 

Relevant academic research and scientific papers

Studies on the total synthesis of disorazole C1. An advanced macrocycle intermediate

Synthesis of protected tetradehydro-(6,6′-S)-(14,14′-S)-(16,16′-R)-disorazole (3), a potential precursor to the natural product disorazole C1 (1), is described. Key features of this work include (a) an unprecedented sequential 1,5 O → O silyl rearrangement/Horner-Wadsworth-Emmons reaction used to construct 18, (b) a highly convergent Sonogashira reaction between the dienyl iodide 7 and the alkyne 8 to assemble the dienyne monomeric fragment 5, and (c) the selective cyclization of 5 to give either the cyclic monomer 23 or the dimer 3.

The synthesis of the monomeric moiety of disorazole C1

The stereocontrolled synthesis of the monomeric subunit of the macrolide dimer disorazole C1 (1) has been accomplished by convergent coupling of 3 and 4 using the Stille method. (C) 2000 Elsevier Science Ltd.