459145-00-7

Upstream product

• 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 
• 140480-06-4 6,8-Bis-(tert-butyl-dimethyl-silanyloxy)-3-chloromethyl-isochromen-1-one 
• 459144-99-1 6,8-Bis-(tert-butyl-dimethyl-silanyloxy)-3-[(E)-4-[(2S,3R)-3-((S)-2-hydroxy-propyl)-oxiranyl]-4-(4-methoxy-benzyloxy)-but-2-enyl]-isochromen-1-one 
• 459144-94-6 (S)-1-{(2R,3S)-3-[1-(4-Methoxy-benzyloxy)-prop-2-ynyl]-oxiranyl}-propan-2-ol 

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 

Relevant academic research and scientific papers

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.

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.