Construction of the Core Structure of Trichotomone

Hongli Yin; Zhe Meng; Bo Liu

doi:10.1055/s-0035-1562491

Synthesis, Table of Contents

Synthesis 2016; 48(22): 3951-3956
DOI: 10.1055/s-0035-1562491

paper

Construction of the Core Structure of Trichotomone

Hongli Yin

^aKey Laboratory of Green Chemistry & Technology of the Ministry of Education, College of Chemistry, Sichuan University, Chengdu, Sichuan 610064, P. R. of China

,

Zhe Meng

^aKey Laboratory of Green Chemistry & Technology of the Ministry of Education, College of Chemistry, Sichuan University, Chengdu, Sichuan 610064, P. R. of China

,

Bo Liu*

^aKey Laboratory of Green Chemistry & Technology of the Ministry of Education, College of Chemistry, Sichuan University, Chengdu, Sichuan 610064, P. R. of China

^bState Key Laboratory of Natural Medicines, China Pharmaceutical University, Nanjing 210009, P. R. of China Email: chembliu@scu.edu.cn

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Abstract

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Abstract

The catecholic ketal core substructure of trichotomone, a dimeric abietane-type diterpenoid, was constructed. Key elements of the synthesis include an Ullmann condensation between a phenol and phenyl bromide, and the final 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ)-mediated oxidative dearomatization/ketalization reaction.

Key words

total synthesis - diterpenoid - abietane - Ullman condensation - oxidative dearomatization.

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References

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