Publications
87.Total synthesis of (+)-fusarisetin A
Jun Huang, Lichao Fang, Jianxian Gong, Chuangchuang Li, Zhen Yang*
Herein we report the full details of our efforts toward the application of Pauson–Khand reaction for the stereoselective construction of the trans-decalin subunit with a C16 quaternary stereocenter of fusarisetin A, which led to the asymmetric total synthesis of (+)-fusarisetin A. The developed chemistry provides an alternative strategy to the intramolecular Diels–Alder reaction that has been employed for the synthesis of trans-decalin based natural products.
86.Tunable and Chemoselective Syntheses of Dihydroisobenzofurans and Indanones via Rhodium-Catalyzed Tandem Reactions of 2‑Triazole-benzaldehydes and 2‑Triazole-alkylaryl Ketones
Hongjuan Shen, Junkai Fu, Jianxian Gong,* and Zhen Yang*
Two novel rhodium(II)-catalyzed tandem reactions were developed for the synthesis of dihydroisobenzofuran and indanone derivatives from 2-triazole-benzaldehydes and 2-triazole-alkylaryl ketones. Dihydroisobenzofuran derivatives were obtained in good yields with high regioselectivities when alcohols were used as nuclophiles in these reactions, whereas the replacement of the alcohol with water resulted in the diastereoselective formation of highly functionalized indanone derivatives.
85.Palladium-Catalyzed Oxidative Rearrangement of Tertiary Allylic Alcohols to Enones with Oxygen in Aqueous Solvent
Jingjie Li , Ceheng Tan , Jianxian Gong *, and Zhen Yang *
A one-pot procedure for Pd(TFA)2-catalyzed 1,3-isomerization of tertiary allylic alcohols to secondary allylic alcohols followed by a Pd(TFA)2/neocuproine-catalyzed oxidative reaction to β-disubstituted-α,β-unsaturated kenones was developed.
84.Concise Stereoselective Synthesis of Oxaspirocycles with 1-Tosyl-1,2,3-triazoles: Application to the Total Syntheses of (±)-Tuberostemospiroline and (±)-Stemona-lactam R
Junkai Fu, Hongjuan Shen, Yuanyuan Chang, Prof. Dr. Chuangchuang Li, Dr. Jianxian Gong and Prof. Dr. Zhen Yang*
• Highlighted in Org. Chem. Highlights, May, 11th, 2015.
A 4-substituted-1-tosyl-1,2,3-triazole-based stereoselective synthesis of structurally diverse oxaspirocycles is reported. The synthesis involves Rh-catalyzed loss of nitrogen from 4-substituted-1-tosyl-1,2,3-triazoles, Grignard reaction, and a ring-closing metathesis reaction as key steps. By employing readily available and stable 4-substituted-1-tosyl-1,2,3-triazoles as surrogates of diazo compounds and nitrogen sources, two types of oxaspirocycles were obtained. The latter compounds, which contain adjacent nitrogen stereocenters, could serve as the core structures of many natural products. This chemistry has been successfully applied to the total syntheses of (±)-tuberostemospiroline and (±)-stemona-lactam R.
83.Total Synthesis of Aplykurodinone-1
Gang Liu, Guangjian Mei, Runwen Chen, Haina Yuan, Zhen Yang*, and Chuang-chuang Li*
The concise total synthesis of aplykurodinone-1 with an unusual cis-fused hydrindane moiety has been accomplished without the need for any protecting group chemistry using a unique SmI2 mediated reductive cascade cyclization reaction and a direct cuprate mediated 1,4-addition. This work represents the first example of the use of a SmI2-mediated intramolecular cascade cyclization reaction between “halide, alkene and aldehyde” groups.
