139684-72-3

Upstream product

• 1501971-59-0 (2R,3S,4R)-1-((R)-4-benzyl-2-oxooxazolidin-3-yl)-2,4-dimethyl-1-oxohexan-3-yl-4-methylbenzenesulfonate 

Downstream Products

• 1309567-83-6 4-methoxy-5-(4-((4-methoxybenzyl)oxy)phenyl)-3-((2E,4E,6R,8R)-4,6,8-trimethyldeca-2,4-dienoyl)pyridin-2(1H)-one 
• 1309567-84-7 4-methoxy-5-(4-((4-methoxybenzyl)oxy)phenyl)-3-((2E,4E,6E,8R,10R)-6,8,10-trimethyldodeca-2,4,6-trienoyl)pyridin-2(1H)-one 
• 1309567-72-3 4-hydroxy-5-(4-hydroxyphenyl)-3-((2E,4E,6R,8R)-4,6,8-trimethyldeca-2,4-dienoyl)pyridin-2(1H)-one 
• 197631-20-2 epipyrone A 
• 1616376-51-2 (2S)-methyl 2-phenyl-2-((2S,4S,6S)-2,4,6-trimethyloctanamido)-acetate 
• 1616376-50-1 (2R)-methyl 2-phenyl-2-((2S,4S,6S)-2,4,6-trimethyloctanamido)acetate 
• 1616376-36-3 (4R)-4-benzyl-3-((2S,4S,6S)-2,4,6-trimethyloctanoyl)oxazolidin-2-one 

Relevant academic research and scientific papers

Directed orthometalation and the asymmetric total synthesis of N -deoxymilitarinone A and torrubiellone B

A diverted total synthesis (DTS) approach to the total synthesis of pyridone alkaloids N-deoxymilitarinone A (8) and torrubiellone B (10) has been developed. The common intermediate 14 was first assembled by a dual directed orthometalation process using a methoxymethyl group as directed metalation group. Other crucial steps include the assembly of polyenes under aldol condensation for DTS using general and concise strategy and diastereoselective synthesis of the syn-dimethyl array by an Evans aldol reaction.

Collective synthesis of 4-hydroxy-2-pyridone alkaloids and their antiproliferation activities

A collective synthesis of 4-hydroxy-2-pyridone alkaloids - specifically, pretenellin B, prebassianin B, farinosone A, militarione D, pyridovericin, and torrubiellone C - has been achieved. Key steps include using a strategic convergent method to synthesize the densely substituted pyridone key intermediate by Suzuki-Miyaura cross-coupling reaction, a divergent synthesis approach of target molecules by aldol condensation of pyridone intermediate with homologous aldehydes, and an iterative synthesis of homologous aldehydes with all-trans-polyene backbones. Interestingly, among the six tumor cell lines investigated, torrubiellone C was found to induce potent and apoptotic inhibitory activities on Jurkat T cells with IC50 values of 7.05 μM. Hence, this approach could potentially contribute to the synthesis of bioactive small-molecule libraries as well as drug discovery.