612846-85-2

Upstream product

• 99493-25-1 diisopropyl (R,R)-2-allyl-1,3,2-dioxaborolane-4,5-dicarboxylate 
• 612846-83-0 ((2S,4R,5R)-4-Allyl-5-methyl-2-phenyl-[1,3]dioxan-5-yl)-methanol 
• 99493-25-1 diisopropyl 2-allyl-1,3,2-dioxaborolane-4,5-dicarboxylate (tartrate allylboronate) 

Downstream Products

• 612846-89-6 (E)-4-[(2R,4S,5S,6R)-6-(5,5-Dimethyl-[1,3]dioxan-2-ylmethyl)-4-(4-methoxy-benzyloxy)-5-methyl-5-triisopropylsilanyloxymethyl-tetrahydro-pyran-2-yl]-but-3-en-1-ol 
• 612846-86-3 Benzoic acid (2R,4S,5S,6R)-6-allyl-4-(4-methoxy-benzyloxy)-5-methyl-5-triisopropylsilanyloxymethyl-tetrahydro-pyran-2-ylmethyl ester 
• 612846-87-4 [(2R,4S,5S,6R)-6-(5,5-Dimethyl-[1,3]dioxan-2-ylmethyl)-4-(4-methoxy-benzyloxy)-5-methyl-5-triisopropylsilanyloxymethyl-tetrahydro-pyran-2-yl]-methanol 
• 1027042-05-2 (2R,4S,5S,6R)-6-(5,5-Dimethyl-[1,3]dioxan-2-ylmethyl)-4-(4-methoxy-benzyloxy)-5-methyl-5-triisopropylsilanyloxymethyl-tetrahydro-pyran-2-carbaldehyde 
• 612846-81-8 (4R,5R,6S)-6-(4-Methoxy-benzyloxy)-5-methyl-5-triisopropylsilanyloxymethyl-nona-1,8-dien-4-ol 

Relevant academic research and scientific papers

Stereoselective total synthesis of the natural (+)-lasonolide A

The natural (+)-lasonolide A (1), an anti-tumor agent, has been synthesized via thermodynamic benzylidene formation at the C22 quaternary chiral center, use of a disulfone equivalent for elongation of the C 15-C17 three-carbon chain as well as introduction of the two trans olefins at C15 and C17, iodocyclization for the upper THP, Michael addition for the bottom THP, and intramolecular Horner-Emmons olefination for the 20-membered macrolactone.

A stereoselective synthesis of the C15-C25 subunit of (+)-lasonolide A

The C15-C25 upper THP segment 2 of (+)-lasonolide A has been synthesized efficiently via diastereomeric differentiation, iodocyclization and Julia-Kocieński's sulfone olefination to install its quaternary chiral center, cis-2,6-disubstituted THP and trans-olefin, respectively.