405297-46-3

Upstream product

• 185841-12-7 (1Z,3E)-5-[(1,1-dimethylethyl)dimethylsilyl]oxy-1,3-pentadienyl butyl telluride 
• 405297-45-2 (2R,4R,R_S)-4,5-epoxy-2-hydroxypentyl p-tolyl sulfoxide 
• 405297-44-1 (2R,4R,R_S)-5-chloro-4-[(1,1-dimethylethyl)dimethylsilyl]oxy-2-hydroxypentyl p-tolyl sulfoxide 
• 405297-43-0 (4R,R_S)-5-chloro-4-[(1,1-dimethylethyl)dimethylsilyl]oxy-2-oxopentyl p-tolyl sulfoxide 
• 18162-48-6 tert-butyldimethylsilyl chloride 
• 88832-56-8 (E)-5-[(1,1-dimethylethyl)dimethylsilyl]oxypent-3-en-1-yne 
• 35042-52-5 (E)-2-penten-4-yn-1-ol 

Downstream Products

• 405297-47-4 (6Z,8E)-(2R,4S,R_S)-10-[(1,1-dimethylethyl)dimethylsilyl]oxy-2,4-isopropylidenedioxy-6,8-decadienyl p-tolyl sulfoxide 
• 405297-63-4 Benzoic acid (R)-2-benzenesulfonyl-1-((E)-2-{(4R,6S)-6-[(2Z,4E)-6-(tert-butyl-dimethyl-silanyloxy)-hexa-2,4-dienyl]-2,2-dimethyl-[1,3]dioxan-4-yl}-vinyl)-6-triisopropylsilanyloxy-heptyl ester 
• 405297-54-3 (2E,4Z,10E,12E)-(7S,9R,17R)-1-[(1,1-dimethylethyl)silyl]oxy-7,9-isopropylidenedioxy-12-(phenylsulfonyl)-17-[tris(1-methylethyl)silyl]oxyoctadeca-2,4,10,12-tetraene 

Relevant academic research and scientific papers

Stereocontrolled synthesis of (-)-macrolactin A

The total synthesis of (-)-macrolactin A, a 24-membered macrolide, has been achieved using a newly developed 1,3-diol synthon for the introduction of two key stereogenic centers. The synthon was derived from sequential use of the Noyori asymmetric reduction followed by chiral sulfoxide methodology. Tellurium-derived cuprate organometallics offered an efficient and highly stereoselective means for installation of the C8 Z/E-diene, while the C15 E/E-segment was derived from a Julia-Lythgoe olefination. Yamaguchi lactonization was used to secure the macrocycle in a convergent approach with the longest linear sequence of 19 steps from Noyori alcohol 6.