760210-72-8

Upstream product

• 149776-79-4 (Z)-1-(trimethylsilyl)-6-(triisopropylsilyl)hex-3-ene-1,5-diyne 
• 760210-71-7 (Z)-(1S,2S,4S)-triisopropyl-[7-methoxymethoxy-7-(2-phenyl-[1,3]dioxan-4-yl)hept-1,5-diynyl]silane 
• 760210-66-0 (Z,Z)-(3S,4S)-1-benzyloxy-4-methoxymethoxy-10-triisopropylsilanyl-deca-5,7-dien-9-yn-3-ol 
• 760210-67-1 (Z,Z)-(1S,2S,4S)-triisopropyl-[7-methoxymethoxy-7-(2-phenyl-[1,3]dioxan-4-yl)hept-1,5-dien-1-ynyl]silane 
• 760210-70-6 (Z)-(1S,2S,4S)-1-(2-phenyl-[1,3]dioxan-4-yl)-7-triisopropylsilanyl-hept-4-en-2,6-diyn-1-ol 
• 760210-73-9 5-(benzyloxy)-2,2-dimethyl-4H-benzo[d][1,3]dioxin-4-one 
• 154714-19-9 5-hydroxy-2,2-dimethyl-4H-benzo[d][1,3]dioxin-4-one 
• 149776-81-8 (Z)-hex-3-en-1,5-diynyl-triisopropylsilane 
• 100-39-0 benzyl bromide 
• 760210-91-1 2-Benzyloxy-6-hydroxy-benzoic acid (3Z,5Z)-(1S,2S)-1-(2-benzyloxy-ethyl)-2-methoxymethoxy-8-triisopropylsilanyl-octa-3,5-dien-7-ynyl ester 

Relevant academic research and scientific papers

Formal total synthesis of oximidine II via a Suzuki-type cross-coupling macrocyclization employing potassium organotrifluoroborates

A formal total synthesis of oximidine II has been achieved, employing a Suzuki-type coupling approach to construct the highly strained, polyunsaturated 12-membered macrolactone. To achieve this goal, benefit was derived from the stability of potassium alkenyltrifluoroborates to establish conditions for the macrocyclization. The stereocontrolled formation of the cis-1,2-diol subunit was accomplished using a diastereoselective, reagent controlled addition to a chiral aldehyde utilizing the Carreira protocol. Advantage was taken of the Snieckus hydroborating reagent to gain access to the key trifluoroborate needed for the macrocyclization.