ABSTRACT: Trioxacarcins DC-45-A2, DC-45-A1, A, D, C7ˊˊ-epi-C and C have been synthesized through stereoselective strategies involving BF3·Et2O-catalyzed ketone-epoxide opening and gold-catalyzed glycosidation reactions, and the full structural assignment of trioxacacin C was deciphered via the syntheses of both its C7ˊˊ-epimers. The gathered knowledge sets the foundation for the design, synthesis and biological evalution of analogs of these natural products as potential payloads for antibody drug conjugates (ADCs) and other delivery systems for targeted and personalized cancer chemotherapy.

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Email: quantsaisky@hotmail.com

EDUCATION BACKGROUND

2003.9 – 2007.7: B.S. in Pharmaceutics Prof. Wen-Hu Duan, Prof. Feng Gao

East China University of Science and Technology (ECUST), Shanghai, P. R. China

2007.9 – 2012.7: Ph.D. in Organic Chemistry Prof. Shu-Li You

State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic

Chemistry (SIOC), Chinese Academy of Sciences (CAS), Shanghai, P. R. China

RESEARCH EXPERIENCES

Rice University, Houston, TX (2013.8 – present)
Total synthesis, full structural assignment and SAR studies of anticancer natural products
trioxacarcins DC-45-A2, DC-45-A1, A, D and C. Postdoctoral research under the direction of Prof. K. C. Nicolaou.
The Scripps Research Institute, La Jolla, CA (2012.9 – 2013.7)
Studies on the total synthesis of maitotoxin, trioxacarcin A. Postdoctoral research under the direction of Prof. K. C. Nicolaou.
Shanghai Institute of Organic Chemistry (SIOC), Chinese Academy of Sciences (CAS), Shanghai, P. R. China (2007.9 – 2012.7)
Cascade reaction development for the efficient asymmetric synthesis of bioactive polycyclic indoles and indolines. Graduate study under the direction of Prof. Shu-Li You.

HONORS AND AWARDS
The Excellent Achievement Awards of Shanghai Graduate Students (Thesis) in 2014
CAS (Chinese Academy of Sciences) The Best Thesis (top 1%) in 2013
CAS (Chinese Academy of Sciences) Excellent Graduate Prize (top 2%) in 2012
CAS (Chinese Academy of Sciences) Special Prize of President Schlorship (top 1%) in 2012
The First Prize of GSK (GlaxoSmithKline) Scholarship in 2010
CAS (Chinese Academy of Sciences) Excellent Student Prize in 2010

PUBLICATIONS
15. K. C. Nicolaou*, Quan Cai, Hongbao Sun, Bo Qin. Total Synthesis of Trioxacarcins DC-45-A1, A, D, C and C7ˊˊ-epi-C and Full Structural Assignment of Trioxacarcin C. J. Am. Chem. Soc. Submitted.
14. K. C. Nicolaou*, Quan Cai, Hongbao Sun, Bo Qin, Mette T. Peterson, Remi J. T. Mikkelsen. Total Synthesis and Biological Evaluation of Trioxacarcins and Analogues Thereof. Manuscript in
preparation.
13. K. C. Nicolaou*, Quan Cai, Bo Qin, Mette T. Peterson, Remi J. T. Mikkelsen, Philipp Heretsch. Total Synthesis of Trioxacarcin DC-45-A2. Angew. Chem. Int. Ed. 2015, 54, 3074.
14. Quan Cai, Qin Yin, Shu-Li You*. Chiral Amine Catalyzed Asymmetric Bromocyclization of
Trptamine Derivatives. Asian. J. Org. Chem. 2014, 3, 408.
15. K. C. Nicolaou*, Ruocheng Yu, Lei Shi, Quan Cai, Min Lu, Phillip Heretsch. General Synthetic Approach to Functionalized Dihydrooxepines. Org. Lett. 2013, 15, 1994.
16. Quan Cai, Xiao-Wei Liang, Shou-Guo Wang, Shu-Li You*. An olefin isomerization/asymmetric Pictet–Spengler cascade via sequential catalysis of ruthenium alkylidene and chiral phosphoric acid. Org. Biomol. Chem. 2013, 11, 1602.
17. Jun-Wei Zhang, Quan Cai, Qin Gu, Xiao-Xin Shi, Shu-Li You*. Enantioselective Synthesis of Benzofurans and Benzoxazines via an Olefin Cross-Metathesis/Intramolecular Oxo-Michael Reaction. Chem. Commun. 2013, 49, 7750.
18. Quan Cai, Xiao-Wei Liang, Shou-Guo Wang, Jun-Wei Zhang, Xiao Zhang, Shu-Li You*. Ring-Closing Metathesis/Isomerization/Pictet–Spengler Cascade via Ruthenium/Chiral Phosphoric Acid Sequential Catalysis. Org. Lett. 2012, 14, 5022.
19. Quan Cai, Chuan Liu, Xiao-Wei Liang, Shu-Li You*. Construction of Pyrroloindolines via Chiral Phosphoric Acid Catalyzed Cascade Michael Addition–Cyclization of Tryptamines. Org. Lett. 2012, 14, 4588.
20. Quan Cai, Shu-Li You*. Organocatalyzed Enantioselective Formal [4 + 2] Cycloaddition of 2,3-Disubstituted Indole and Methyl Vinyl Ketone. Org. Lett. 2012, 14, 3040.
21. Quan Cai, Chao Zheng, Jun-Wei Zhang, Shu-Li You*. Enantioselective Michael/Mannich
Polycyclization Cascade of Indolyl Enones Catalyzed by Quinine-Derived Primary Amines. Angew.Chem. Int. Ed. 2011, 50, 8665. (Highlighted by ACIE, 2011, 51, 46)
22. Jun-Wei Zhang, Quan Cai, Xiao-Xin Shi, Wei Zhang, Shu-Li You*. Enantioselective Synthesis of Tetrahydropyrano[3,4-b] Indoles Catalyzed by Chiral N-Triflyl Phosphoramide via Intramolecular Friedel-Crafts Alkylation Reaction. Synlett 2011, 1239. (Invited Cluster “Brønsted Acid Catalysis”)
23. Quan Cai, Chao Zheng, Shu-Li You*. Enantioselective Intramolecular Aza-Michael Addition of Indoles Catalyzed by Chiral Phosphoric Acid. Angew. Chem. Int. Ed. 2010, 49, 8666. (Highlighted by Synfacts, 2010, 12, 1428; Synfacts of the month)
24. Quan Cai, Zhuo-An Zhao, Shu-Li You*. Asymmetric Construction of Polycyclic Indoles through Olefin Cross-Metathesis/ Intramolecular Friedel-Crafts Alkylation under Sequential Catalysis. Angew.Chem. Int. Ed. 2009, 48, 7428. (Highlighted by Synfacts, 2009, 9, 1375)
25. Shu-Li You*, Quan Cai, Mi Zeng. Chiral Brønsted Acids Catalyzed Friedel-Crafts Alkylation
Reaction. Chem. Soc. Rev. 2009, 38, 2190.