880145-46-0

Upstream product

• 858676-59-2 (2E)-3-[benzyl(dimethyl)silyl]acrylaldehyde 
• 61550-02-5 (furan-2-yloxy)-trimethylsilane 
• 1631-70-5 benzyldimethylsilane 
• 729603-57-0 (2E)-3-[benzyl(dimethyl)silyl]prop-2-en-1-ol 

Downstream Products

• 880145-47-1 (5R)-5-{(1S)-1-[benzyl(dimethyl)silyl]-4,4-dibromobut-3-en-1-yl}furan-2(5H)-one 
• 880145-51-7 diethyl {(3S,3aR,7S,7aR)-7-[benzyl(dimethyl)silyl]-2-oxo-4-vinyl-2,3,3a,6,7,7a-hexahydro-1-benzofuran-3-yl}phosphonate 
• 880145-54-0 (1R,2R,6S)-6-[benzyl(dimethyl)silyl]-2-[(1S,2S)-1-(hydroxymethyl)-2-methylbut-3-en-1-yl]-3-vinylcyclohex-3-en-1-ol 
• 880145-53-9 (3S,3aR,7S,7aR)-7-[benzyl(dimethyl)silyl]-3-[(1S)-1-methylprop-2-en-1-yl]-4-vinyl-3a,6,7,7a-tetrahydro-1-benzofuran-2(3H)-one 
• 880145-52-8 (3Z,3aS,7S,7aR)-7-[benzyl(dimethyl)silyl]-3-ethylidene-4-vinyl-3a,6,7,7a-tetrahydro-1-benzofuran-2(3H)-one 
• 880145-55-1 (1R,2S,7S,8S,8aR)-2-[benzyl(dimethyl)silyl]-8-(hydroxymethyl)-7-methyl-1,2,3,7,8,8a-hexahydronaphthalen-1-ol 
• 880145-50-6 (3aR,7S,7aR)-7-[benzyl(dimethyl)silyl]-4-vinyl-3a,6,7,7a-tetrahydro-1-benzofuran-2(3H)-one 
• 880145-48-2 (3aS,7S,7aR)-7-[benzyl(dimethyl)silyl]-4-bromo-3a,6,7,7a-tetrahydro-1-benzofuran-2(3H)-one 

Relevant academic research and scientific papers

Formal enantioselective synthesis of (+)-compactin

The challenging structural features and important biological activity of (+)-compactin (1) explain the substantial synthetic interest that it has generated. We report a novel enantioselective approach to the advanced intermediate 2a, which constitutes a formal synthesis of (+)-1. The sequence utilizes MacMillan's organocatalytic Mukaiyama-Michael reaction, which stereoselectively adds the silyloxyfuran 6 to α,β-unsaturated aldehyde 7. The chirality generated in this reaction guides the formation of the other three consecutive stereocenters found in 2a.