中文
Earlier issues
Announcement
More
Progress in Chemistry 2010, Vol. 22 Issue (04): 537-556   Next Articles

• Invited Article •

The Study of Resource Chemistry

Tian Weisheng**; Shi Yong   

  1. ( Key Laboratory of Synthetic Chemistry of Natural Substances, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032, China)
  • Received: Revised: Online: Published:
  • Contact: Tian Weisheng E-mail:wstian@sioc.ac.cn
PDF ( 2084 ) Cited
Export

EndNote

Ris

BibTeX

This review summarize our research progress in resource chemistry, which related to the reaction of steroidal sapogenin (natural resource compound) and fluoroalkanosulfonyl fluoride (non-natural one) as well as their application in organic synthesis. The strategies and tactics of utilizing steroidal sapogenin in “atom economy” way are introduced in the first paragraph. For solving the environmental pollution and resource waste generated in the industrial utilization of steroidal sapogenin, our group developed new method that using 30% commercial H2O2 instead of CrO3 to oxidize pseudo-sapogenin, which made it is possible to the 100% utilization of the steroidal sapogenin resource. Direct oxidization of steroidal sapogenin with the per-acid generated in situ starting from 30% commercial H2O2 and acid to produce pregna-16,20-diol type compound and 4R-methyl δ-valerolactone. Iodine induced abnormal Baeyer-Villiger rearrangement of sapogenin provided steroidal 16-hydroxyl-22-lactone and 3R-methyl γ-butyrolactone. All of their degraded products have been applied in the synthesis of some steroidal medicine, insect hormone, perfume and natural product. The strategy of using intact skeleton of steroidal sapogenin to synthesize target molecule are also described. In second paragraph, the strategies and tactics of utilizing fluoroalkanosulfonyl fluoride are introduced. To make reaction symbiosis is a new ideal in order to enhance the utilization ratio of the resource compound. We explore symbiotic reactions of vicinal diol epoxidation, alkene epoxidation and carbocation rearrangement with fluoroalkanosulfonyl fluoride hydrolysis based on this concept. The synthetic application of such reactions is also presented in this review.

Contents
1 Resource chemistry and resource compound
2 Resource chemistry based on natural resource compound steroidal sapogenin
2.1 Steroidal sapogenin: origination, utilizing way and problems remained
2.2 The clean oxidative degradation of steroidal sapogenin
2.3 The reaction of the degradation products of steroidal sapogenin and their application in organic synthesis
2.4 The synthesis of natural sterols by using the intact skeleton of steroidal sapogenin
3 Resource chemistry based on non-natural resource fluoroalkanosulfonyl fluoride
3.1 The reaction of fluoroalkanosulfonyl fluoride and its application in Epristeride synthesis
3.2 The symbiotic reaction of fluoroalkanosulfonyl fluoride hydrolysis and 1,2-diol epoxidation
3.3 The symbiotic reaction of fluoroalkanosulfonyl fluoride hydrolysis and alkene epoxidation
3.2 The symbiotic reaction of fluoroalkanosulfonyl fluoride hydrolysis and carbocation rearrangement

Key words: resource chemistry, steroidal sapogenin, fluoroalkanosulfonyl fluoride, symbiotic reaction, natural product, 4R-methyl δ-valerolactone

CLC Number: 

［1 ］ 田伟生( Tian W S) . 科学新闻周刊( Science News Weekly) ，1999，5: 13
［2 ］ Marker R E，Rohrmann E. J. Am. Chem. Soc. ，1939，61:3592—3593
［3 ］ Sato K，Aoki M，Noyori R. Science，1998，281: 1646—1647
［4 ］ Xi Z W，Zhou N，Sun Y，et al. Science，2001，292: 1139—1141
［5 ］ 田伟生( Tian W S) ，刘闪闪( Liu S S) ，沈军伟( Shen J W) .CN 1146574C，1996
［6 ］ 田伟生( Tian W S) ，刘闪闪( Liu S S) ，邱丙开( Qiu B K) .CN 1221563C，2003
［7 ］ 田伟生( Tian W S) . CN 1061985C，1996
［8 ］ 田伟生( Tian W S ) ，李民( Li M ) ，殷海峰( Yin H F ) .CN1120844C，2001
［9 ］ 汪君(Wang J) . 中国科学院上海有机化学研究所硕士学位论文( Master Dissertation of Shanghai Institute of Organic Chemistry，Chinese Academy of Sciences) ，2005
［10］ Marker R E，Turner D L. J. Am. Chem. Soc. ，1940，62:2540—2541
［11］ 朱臻( Wang Z ) . 中国药科大学博士学位论文( Doctoral Dissertation of China Pharmaceutical University) ，1996
［12］ 陈玲( Cheng L) . 中国科学院上海有机化学研究所博士学位论文( Doctoral Dissertation of Shanghai Institute of Organic Chemistry，Chinese Academy of Sciences) ，2000
［13］ 张东山( Zhang D S) . 中国科学院上海有机化学研究所博士学位论文(Doctoral Dissertation of Shanghai Institute of Organic Chemistry，Chinese Academy of Sciences) ，2005
［14］ 林静容( Lin J R) ，王静(Wang J) ，陈丽君( Chen L J) . 化学学报(Acta Chem. Sinica) ，2006，64(12) : 1265—1268
［15］ 林静容( Lin J R) ，贾世风( Jia S F) ，周南琰( Zhou N Y) . 化学学报(Acta Chem. Sinica) ，2008，66: 2637—2645
［16］ Lin J R，Zhou N Y，Jiang S F，et al. Tetrahedr. Lett. ，2007，48: 4987—4989
［17］ 周南琰( Zhou N Y) . 上海师范大学硕士学位论文( Master Dissertation of Shanghai Normal University) ，2008
［18］ Pettit G R，Inoue M，Kamano Y，et al. J. Am. Chem. Soc. ，1988，110(6) : 2006—2007
［19］ LaCour T G，Guo C，Fuchs P L，et al. J. Am. Chem. Soc. ，1998，120(4) : 692—707
［20］ 贾兰齐( Jia L Q) . 中国科学院上海有机化学研究所博士学位论文( Doctoral Dissertation of Shanghai Institute of Organic Chemistry，Chinese Academy of Sciences) ，2002
［21］ 肖晴(Xiao Q) . 中国科学院上海有机化学研究所博士学位论文( Doctoral Dissertation of Shanghai Institute of Organic Chemistry，Chinese Academy of Sciences) ，2005
［22］ Redpath J，Zeelen F J. Chem. Soc. Rev. ，1983，12: 75—98
［23］ Sarma N S，Krishna M S，Pasha S G，et al. Chem. Rev. ，2009，109(6) : 2803—2828
［24］ Maria V，D’Auria L，Minale R，et al. Chem. Rev. ，1993，93:1839—1895
［25］ 李民( Li M) . 中国科学院上海有机化学研究所博士学位论文( Doctoral Dissertation of Shanghai Institute of Organic Chemistry，Chinese Academy of Sciences) ，2001
［26］ 汤小虎( Tang X H) . 中国科学院上海有机化学研究所博士学位论文( Doctoral Dissertation of Shanghai Institute of Organic Chemistry，Chinese Academy of Sciences) ，2003
［27］ 王涛(Wang T) . 中国科学院上海有机化学研究所博士学位论文( Doctoral Dissertation of Shanghai Institute of Organic Chemistry，Chinese Academy of Sciences) ，2004
［28］ Zhou W S，Tian W S. Tetrahedr. ，1987，43: 3705—3712
［29］ Grove M D，Spencer G F，Rohwedder W K，et al. Nature，1979，281: 216—217
［30］ Kubo S，Mimaki Y，Terao M，et al. Phytochem. ，1992，31:3969 － 3973
［31］ 李恒( Li H) . 重楼属植物( Paris Genus Plant) ，北京: 科学出版社( Beijing: Science Press) ，1998，158—162
［32］ Wang W，Hong J，Lee C，et al. J. Nat. Prod. ，2004，67:584—591
［33］ 沈凯圣( Shen K S) . 中国科学院上海有机化学研究所博士学位论文( Doctoral Dissertation of Shanghai Institute of Organic Chemistry，Chinese Academy of Sciences) ，2007
［34］ 史勇( Shi Y) . 中国科学院上海有机化学研究所博士学位论文( Doctoral Dissertation of Shanghai Institute of Organic Chemistry，Chinese Academy of Sciences) ，2009
［35］ 李涛( Li T) ，黄贤贵(Huang X G) ，林静容( Lin J R) . 化学学报(Acta Chem. Sinica) ，2007，65: 1165—1171
［36］ 王子坤(Wang Z K) ，田伟生( Tian W S) ，潘鑫复( Pan X F) .有机化学(Org. Chem. ) ，2007，27: 866—869
［37］ 王子坤( Wang Z K ) . 兰州大学博士学位论文( Doctoral Dissertation of Lanzhou University) ，2007
［38］ 沈伟( Shen W) . 中国科学院上海有机化学研究所博士学位论文( Doctoral Dissertation of Shanghai Institute of Organic Chemistry，Chinese Academy of Sciences) ，2009
［39］ 张永霞( Zhang Y X) . 中国科学院上海有机化学研究所硕士学位论文( Master Dissertation of Shanghai Institute of Organic Chemistry，Chinese Academy of Sciences) ，2009
［40］ 沈军伟( Shen J W) . 中国科学院上海有机化学研究所博士学位论文( Doctoral Dissertation of Shanghai Institute of Organic Chemistry，Chinese Academy of Sciences) ，2008
［41］ Guo C，Fuchs P. Tetrahedr. Lett. ，1998，39: 1099—1102
［42］ Yu W，Jin Z. J. Am. Chem. Soc. ，2002，124: 6576—6583
［43］ Tian W S，Guan H P，Pan X F. Chin. J. Chem. ，2003，21:784—788
［44］ 杨庆雄(Yang Q X) ，田伟生( Tian W S) ，潘嵩( Pan S) . 化学学报(Acta Chem. Sinica) ，2004，62: 2171—2176
［45］ Rincon S，del Rio R E，Sandoval-Ramirez J，et al. Tetrahedr. ，2006，62: 2594—2602
［46］ Frederick C U. J. Org. Chem. ，1962，27: 656—658
［47］ Xu Q H，Peng X W，Tian W S. Tetrahedr. Lett. ，2003，44:9375 － 9377
［48］ 许启海(Xu Q H) . 中国科学院上海有机化学研究所博士学位论文( Doctoral Dissertation of Shanghai Institute of Organic Chemistry，Chinese Academy of Sciences) ，2004
［49］ Qin H J，Tian W S，Lin C W. Tetrahedr. Lett. ，2006，46:3217 － 3419
［50］ Chen L J，Xu Q H，Huang H，et al. Tetrahedr. Lett. ，2007，47: 3475 － 3477
［51］ 田伟生( Tian W S) ，许启海(Xu Q H) ，陈玲( Chen L) . 中国科学，B 辑化学( Chinese Science in China Ser. B Chemistry) ，2004，47: 142—144
［52］ 陈丽君( Chen L J) . 上海师范大学硕士学位论文( Master Dissertation of Shanghai Normal University) ，2007
［53］ 唐小枚( Tang X M) ，许启海(Xu Q H) ，王静(Wang J) . 化学学报(Acta Chem. Sinica) ，2007，65: 2315—2319
［54］ Zhu Z，Tian W S，Liao Q J. Tetrahedr. Lett. ，1996，37:8553—8556
［55］ Zhu Z，Tian W S，Liao Q J. Bioorg. Med. Chem. Lett. ，1998，8: 1949—1952
［56］ 严兆华(Yan Z H) . 中国科学院上海有机化学研究所博士学位论文( Doctoral Dissertation of Shanghai Institute of Organic Chemistry，Chinese Academy of Sciences) ，1999
［57］ Yan Z H，Wang J Q，Tian W S. Tetrahedr. Lett. ，2003，44:9383—9384
［58］ Yan Z H，Tian W S. Tetrahedr. Lett. ，2004，45: 2211—2213
［59］ 雷震( Lei Z) . 中国科学院上海有机化学研究所硕士学位论文( Master Dissertation of Shanghai Institute of Organic Chemistry，Chinese Academy of Sciences) ，1997
［60］ Chen L，Ding K，Tian W S. Chem. Commun. ，2003，838—839
［61］ 丁凯(Ding K) . 中国科学院上海有机化学研究所博士学位论文( Doctoral Dissertation of Shanghai Institute of Organic Chemistry，Chinese Academy of Sciences) ，1999
［62］ 孙云山( Sun Y S) . 中国科学院上海有机化学研究所博士学位论文( Doctoral Dissertation of Shanghai Institute of Organic Chemistry，Chinese Academy of Sciences) ，1999
[1] Xiaoxiao Wu, Kaiqing Ma. Total Synthesis of Stemona Alkaloids [J]. Progress in Chemistry, 2020, 32(6): 752-760.
[2] Luo Shipeng, Huang Peiqiang. Malic acid——A Versatile Chiral Building Block in the Enantioselective Total Synthesis of Natural Products and in Synthetic Methodologies [J]. Progress in Chemistry, 2020, 32(11): 1846-1868.
[3] Kangkang Zhi, Xin Yang. Natural Product Gels and Their Gelators [J]. Progress in Chemistry, 2019, 31(9): 1314-1328.
[4] Yuxia Gao, Yun Liang, Jun Hu, Yong Ju. Supramolecular Chiral Self-Assembly Based on Small Molecular Natural Products [J]. Progress in Chemistry, 2018, 30(6): 737-752.
[5] Xiaoyu Liu, Tao Xiao, Yong Qin. Total Synthesis of the Akuammiline Alkaloid Strictamine [J]. Progress in Chemistry, 2018, 30(5): 578-585.
[6] Tingting Huang, Zihua Zhou, Qi Liu, Xiaozheng Wang, Wenli Guo, Shuangjun Lin*. Biosynthetic Mechanisms of Alkaloids from Actinomycetes [J]. Progress in Chemistry, 2018, 30(5): 692-702.
[7] Xu Lining, Zhang Juntao, Tao Cheng, Cao Xiaoping. Advances in the Synthesis of Vinyl Chloride Compounds [J]. Progress in Chemistry, 2013, 25(11): 1876-1887.
[8] Wu Jindan, Ju Yong. Molecular and Ion Recognition Molecules Based on Natural Products [J]. Progress in Chemistry, 2013, 25(11): 1888-1897.
[9] Song Gao, Sumit Basu, Guangyi Yang, Arijita Deb, Ming Hu. Oral Bioavailability Challenges of Natural Products Used in Cancer Chemoprevention [J]. Progress in Chemistry, 2013, 25(09): 1553-1574.
[10] Tong Xing, Xiao Xiaohua, Deng Jianchao, Wang Jiayue, Li Gongke. Applications of Low Temperature Microwave Technique in Chemistry Research [J]. Progress in Chemistry, 2010, 22(12): 2462-2468.
[11] Yang Zhen*. Syntheses of Biological Active Natural Products and Natural Product-Like Molecules [J]. Progress in Chemistry, 2009, 21(01): 47-54.
[12] Ge Huiming|Tan Renxiang**. Symbionts, an Important Source of New Bioactive Natural Products [J]. Progress in Chemistry, 2009, 21(01): 30-46.
[13]

Hu Jinfeng1,2**|Gary R.Eldridge1,Yu Yihua3,Mark O's Neil-Johnson2

. High-throughput Natural Product Chemistry Methods and the Application of the Capillary NMR Probe [J]. Progress in Chemistry, 2008, 20(04): 429-440.
[14] Zhenming Chen1, Jinhua Liu 2, Tao, Junhua2,3**. Biocatalysis for Green Chemistry and Drug Development [J]. Progress in Chemistry, 2007, 19(012): 1919-1927.
[15] Fang Xuexun* Yang Jingang Shi Xiujuan. Matrix Metalloproteinase Inhibitors from Natural Product [J]. Progress in Chemistry, 2007, 19(012): 1991-1998.
Viewed
Full text


Abstract

The Study of Resource Chemistry