281224-85-9

Upstream product

• 328570-79-2 4-methyl-3-(4-hydroxybutyl)anisole 
• 19614-12-1 2-bromo-5-methoxybenzyl bromide 
• 100-84-5 1-methoxy-3-methyl-benzene 
• 328570-78-1 4-(2-bromo-5-methoxy-phenyl)-butan-1-ol 
• 149244-21-3 1-bromo-2-(but-3-en-1-yl)-4-methoxybenzene 

Downstream Products

• 328570-81-6 6-(5-methoxy-2-methyl-phenyl)-1-phenoxy-hexan-3-one 
• 126210-14-8 Astrogorgadiol 
• 328570-85-0 (1R,7aR)-1-((R)-1,5-Dimethyl-hex-4-enyl)-4-[2-(5-methoxy-2-methyl-phenyl)-ethyl]-7a-methyl-1,2,3,6,7,7a-hexahydro-inden-5-one 
• 328570-89-4 (1R,3aS,4S,7aR)-1-((R)-1,5-Dimethyl-hex-4-enyl)-4-[2-(5-methoxy-2-methyl-phenyl)-ethyl]-7a-methyl-octahydro-inden-5-one 
• 328570-91-8 (1R,3aS,4S,5R,7aR)-4-(5-methoxy-2-methylphenethyl)-7a-methyl-1-((R)-6-methylheptan-2-yl)-octahydro-1H-inden-5-ol 
• 328570-87-2 (1R,3aS,4S,7aR)-1-((R)-1,5-Dimethyl-hexyl)-4-[2-(5-methoxy-2-methyl-phenyl)-ethyl]-7a-methyl-octahydro-inden-5-one 
• 1444-59-3 6-(m-methoxyphenyl)hex-1-en-3-one 

Relevant academic research and scientific papers

Synthesis of (-)-astrogorgiadiol

Reaction of Rh2(S)-PTPA4 with the (R)-citronellol-derived α-diazo-β-ketoester 1 led to the formation of cyclic β-ketoester 2 in 95% yield and 48% diastereomeric excess. The purity of 2 was increased to >99% de after one crystallization. To demonstrate its utility in steroid total synthesis, the β-ketoester 2 was carried on to secosteroid (-)-astrogorgiadiol (3), a naturally occuring vitamin D analogue with antiproliferative properties.