Recent advances of intermolecular Diels-Alder reaction in bio-inspired synthesis of natural products

Science China Chemistry

Volumn 57, Issue 7, 2014, Pages 926-929

  Wan, Chunyun ^a,b   Deng, Jun ^b   Liu, Hua ^a   Bian, Ming ^b   Li, Ang ^b  

^a JIANGXI UNIVERSITY OF TRADITIONAL CHINESE MEDICINE   (China)

^b SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY   (China)

Author keywords

bio inspired synthesis; dimerization; intermolecular Diels Alder reaction; terpenoid

Indexed keywords

CHEMISTRY; DIMERIZATION;

BIO-INSPIRED SYNTHESIS; BUILDING BLOCKES; FURTHER DEVELOPMENT; INTERMOLECULAR DIELS-ALDER REACTIONS; NATURAL PRODUCT SYNTHESIS; ORGANIC SYNTHESIS; STERICALLY DEMANDING; TERPENOIDS;

SYNTHESIS (CHEMICAL);

EID: 84903701088     PISSN: 16747291     EISSN: None     Source Type: Journal    
DOI: 10.1007/s11426-014-5144-5     Document Type: Review

References (20)

1. Nicolaou KC, Snyder SA, Montagnon T, Vassilikogiannakis G. The Diels-Alder reaction in total synthesis. Angew Chem Int Ed, 2002, 41: 1668-1698
2. Corey EJ. Catalytic enantioselective Diels-Alder reactions: methods, mechanistic fundamentals, pathways, and applications. Angew Chem Int Ed, 2002, 41: 1650-1667
3. Stocking EM, Williams RM. Chemistry and biology of biosynthetic Diels-Alder reactions. Angew Chem Int Ed, 2003, 42: 3078-3115
4. Takao KI, Munakata R, Tadano KI. Recent advances in natural product synthesis by using intramolecular Diels-Alder reactions. Chem Rev, 2005, 105: 4779-4807
5. Juhl M, Tanner D. Recent applications of intramolecular Diels-Alder reactions to natural product synthesis. Chem Soc Rev, 2009, 38: 2983-2992
6. Roche SP, Porco JA. Dearomatization strategies in the synthesis of complex natural products. Angew Chem Int Ed, 2011, 50: 4068-4093
7. Funel JA, Abele S. Industrial applications of the Diels-Alder reaction. Angew Chem Int Ed, 2013, 52: 3822-3863
8. Nicolaou KC, Hale CRH, Nilewski C, Ioannidou HA. Constructing molecular complexity and diversity: total synthesis of natural products of biological and medicinal importance. Chem Soc Rev, 2012, 41: 5185-5238
9. Nawrat CC, Moody CJ. Quinones as dienophiles in the Diels-Alder reaction: history and applications in total synthesis. Angew Chem Int Ed, 2014, 53: 2056-2077
10. Herout V, Sorm F. Substances of Artemisia absinthium and isolation of crystalline prochamazulenogen. Collect Czech Chem Commun, 1953, 18: 854-869
11. Zhang WH, Luo SJ, Fang F, Chen QS, Hu HW, Jia XS, Zhai HB. Total synthesis of absinthin. J Am Chem Soc, 2005, 127: 18-19
12. Li C, Yu XL, Lei XG. A biomimetic total synthesis of (+)-ainsliadimer A. Org Lett, 2010, 12: 4284-4287
13. Wu ZJ, Xu XK, Shen YH, Su J, Tian JM, Liang S, Li HL, Liu RH, Zhang WD. Ainsliadimer A, a new sesquiterpene lactone dimer with an unusual carbon skeleton from Ainsliaea macrocephala. Org Lett, 2008, 10: 2397-2400
14. Li C, Dian LY, Zhang WD, Lei XG. Biomimetic syntheses of (-)-gochnatiolides A-C and (-)-ainsliadimer B. J Am Chem Soc, 2012, 134: 12414-12417
15. Li C, Dong T, Dian LY, Zhang WD, Lei XG. Biomimetic syntheses and structural elucidation of the apoptosis inducing sesquiterpenoid trimers: (-)-ainsliatrimers A and B. Chem Sci, 2013, 4: 1163-1167
16. Li C, Lei XG. Strategies toward the biomimetic syntheses of oligomeric sesquiterpenoids. J Org Chem, 2014, 79: 3289-3295
17. Xia DL, Du Y, Yi Z, Song H, Qin Y. Total syntheses of ainsliadimer B and gochnatiolides A and B. Chem Eur J, 2013, 19: 4423-4427
18. Bohlmann F, Ahmed M, Jakupovic J, Kinga RM, Robinsona H. Dimeric sesquiterpene lactones and kolavane derivatives from Gochnatia paniculata. Phytochemistry, 1983, 22: 191-195
19. Acebey L, Sauvain M, Beck S, Moulis C, Gimenez A, Jullian V. Bolivianine, a new sesterpene with an unusual skeleton from Hedyosmum angustifolium, and its isomer, Isobolivianine. Org Lett, 2007, 9: 4693-4696
20. Yuan CC, Du B, Yang L, Liu B. Bioinspired total synthesis of Bolivianine: a Diels-Alder/intramolecular Hetero-Diels-Alder cascade approach. J Am Chem Soc, 2013, 135: 9291-9294