880766-68-7

Upstream product

• 74080-50-5 <2R,3R>-3-methyl-4-penten-2-ol 
• 824-94-2 p-methoxybenzyl chloride 
• 880766-65-4 (-)-(2S,3R,4R)-1-tert-butyldiphenylsilyloxy-4,5-isopropylidenedioxy-2-mesyloxy-3-methylpentane 
• 880766-67-6 (-)-(2R,3R,4R)-4-(4-methoxybenzyl)oxy-3-methylpentane-1,2-diol 
• 603040-99-9 (2S,3R)-3-(4-Methoxy-benzyloxy)-2-methyl-butyraldehyde 
• 1779-49-3 Methyltriphenylphosphonium bromide 

Downstream Products

• 603040-99-9 (2S,3R)-3-(4-Methoxy-benzyloxy)-2-methyl-butyraldehyde 
• 880766-71-2 (5R,6R)-5,6-dimethyl-4-(phenylselenylmethyl)tetrahydro-2H-pyran-2-one 
• 139403-50-2 (4R,5R,6R)-5,6-Dimethyl-4-(phenylselanylmethyl)tetrahydro-2H-pyran-2-one 
• 880766-69-8 (2RS)-2-[(1R,2R-)-2-(4-methoxybenzyl)oxy-1-methylpropyl]cyclopropane-1,1-dimethyl dicarboxylate 

Relevant academic research and scientific papers

Chondramide C: Synthesis, configurational assignment, and structure-activity relationship studies

(Chemical Equation Presented) Two solutions for one problem: Of the four isomers of chondramide C synthesized, the two shown in the scheme exhibit nearly the same conformation of the peptide segment and consequently unfold equal biological activities.

Total synthesis of (+)-mycalamide A

A convergent total synthesis of (+)-mycalamide A is described. A Yb(OTf)3-TMSCl catalytic system is used to synthesize a trioxadecalin ring system, which contains the right segment of mycalamide A. In addition, a tetrahydropyran ring, which is

Convergent total synthesis of (+)-mycalamide A

The details of a convergent total synthesis of (+)-mycalamide A are descri7bed. Yb(OTf)3-TMSCl-catalyzed cross-aldol reaction conditions are used to synthesize the right segment of mycalamide A. In this reaction, an acid-sensitive aldehyde reacts with methyl trimethylsilyl dimethylketene acetal without epimerization to provide the desired aldol adduct. Additionally, a tetrahydropyran ring, which is the left segment of mycalamide A, is prepared using a novel one-pot δ-lactone formation methodology. Both segments are constructed from a common starting material, D-mannitol. These segments are then coupled in the presence of BuLi, and the functional groups are transformed to complete the synthesis of (+)-mycalamide A.