459144-99-1

Upstream product

• 140480-06-4 6,8-Bis-(tert-butyl-dimethyl-silanyloxy)-3-chloromethyl-isochromen-1-one 
• 459144-94-6 (S)-1-{(2R,3S)-3-[1-(4-Methoxy-benzyloxy)-prop-2-ynyl]-oxiranyl}-propan-2-ol 
• 459144-91-3 tert-Butyl-((S)-2-{(2R,3S)-3-[1-(4-methoxy-benzyloxy)-prop-2-ynyl]-oxiranyl}-1-methyl-ethoxy)-dimethyl-silane 
• 459144-92-4 1-{(2R,3R)-3-[(S)-2-(tert-Butyl-dimethyl-silanyloxy)-propyl]-oxiranyl}-3-trimethylsilanyl-prop-2-yn-1-ol 
• 459144-93-5 1-{(2R,3R)-3-[(S)-2-(tert-Butyl-dimethyl-silanyloxy)-propyl]-oxiranyl}-prop-2-yn-1-ol 
• 824-94-2 p-methoxybenzyl chloride 
• 7486-35-3 tri-n-butyl(vinyl)tin 

Downstream Products

• 12772-57-5 (9Z,11E)-(4R,6R,8R)-16-Chloro-17,19-dihydroxy-4-methyl-3,7-dioxa-tricyclo[13.4.0.0^6,8]nonadeca-1⁽¹⁵⁾,9,11,16,18-pentaene-2,13-dione 
• 75207-13-5 Monocillin I 
• 459145-00-7 6-(tert-Butyl-dimethyl-silanyloxy)-8-hydroxy-3-[(E)-4-[(2S,3R)-3-((S)-2-hydroxy-propyl)-oxiranyl]-4-(4-methoxy-benzyloxy)-but-2-enyl]-isochromen-1-one 

Relevant academic research and scientific papers

Improvements of the total synthesis of monocillin I and radicicol via Miyaura-Suzuki couplings

The palladium-catalyzed coupling of the vinyldisiamylborane, formed in situ, affords the isocoumarins which can be used further for the synthesis of radicicol and related macrolides, in 72% global overall yield from the alkyne. Advantages over related vinylboronates or vinyltin couplings are discussed in the case of the present examples.

Convergent stereospecific total synthesis of monocillin I and radicicol: Some simplifications and improvements

A much improved and reliable access to the macrolide 9, key-intermediate in our synthesis of monocillin I and radicicol is reported, via a modification of our first synthesis. The formation of the conjugated E,Z-dienone trans-epoxide is now achieved in a much higher yield, in a stereospecific reaction, by elimination of the methanesulfonate ester of the 6′-OH of the intermediate macrolide. It is also shown that the configuration of the 6′-OH has no significant incidence on all the steps leading to 9, and that consequently the two diastereoisomers 12, epimeric at 6′, can be used for the synthesis of radicicol.