Application of two direct C(sp3)-H functionalizations for total synthesis of (+)-lactacystin.
作者： Masayuki Inoue , Shun Yoshioka , Masanori Nagatomo
DOI: 10.1021/OL503291S
关键词: Tetra 、 20s proteasome 、 Intramolecular force 、 Alkynylation 、 Intermolecular force 、 Chemistry 、 Stereochemistry 、 Acylation 、 Lactacystin 、 Total synthesis
摘要: Herein, we report a new synthetic route from (S)-pyroglutaminol to (+)-lactacystin, potent inhibitor of the 20S proteasome. The photoinduced intermolecular C(sp3)–H alkynylation and intramolecular acylation chemo- stereoselectively constructed tetra- trisubstituted carbon centers, respectively. obtained bicycle was transformed into target compound in concise manner. present total synthesis demonstrates power direct functionalizations for assembly multiple functionalized structures natural products.
acs.org
sci-hub.se 参考文章(77)
Chirumarry Sridhar, Bodduri V. D. Vijaykumar, Laghuvarapu Radhika, Dong-Soo Shin, Srivari Chandrasekhar, Asymmetric Formal Synthesis of (+)‐Lactacystin European Journal of Organic Chemistry. ,vol. 2014, pp. 6707- 6712 ,(2014) , 10.1002/EJOC.201402700
Cheol H. Yoon, David L. Flanigan, Kyung S. Yoo, Kyung W. Jung, Stereogenic Evolution ofclasto-Lactacystin β-Lactone fromL-Serine European Journal of Organic Chemistry. ,vol. 2007, pp. 37- 39 ,(2007) , 10.1002/EJOC.200600835
Gerald Pattenden, Gwenaëlla Rescourio, A new synthetic approach to (+)-lactacystin based on radical cyclisation of enantiopure α-ethynyl substituted serine derivatives to 4-methylenepyrrolidinones Organic and Biomolecular Chemistry. ,vol. 6, pp. 3428- 3438 ,(2008) , 10.1039/B806681G
Ljudmila Borissenko, Michael Groll, 20S proteasome and its inhibitors: crystallographic knowledge for drug development. Chemical Reviews. ,vol. 107, pp. 687- 717 ,(2007) , 10.1021/CR0502504
SATOSHI OMURA, TOMOKO FUJIMOTO, KAZUHIKO OTOGURO, KEIICHI MATSUZAKI, RYOZO MORIGUCHI, HARUO TANAKA, YASUHARU SASAKI, Lactacystin, a novel microbial metabolite, induces neuritogenesis of neuroblastoma cells. The Journal of Antibiotics. ,vol. 44, pp. 113- 116 ,(1991) , 10.7164/ANTIBIOTICS.44.113
W. H. Urry, D. J. Trecker, Photochemical Reactions of 1,2-Diketones Journal of the American Chemical Society. ,vol. 84, pp. 118- 120 ,(1962) , 10.1021/JA00860A034
John K. Thottathil, Jerome L. Moniot, Richard H. Mueller, Michael K. Y. Wong, Thomas P. Kissick, Conversion of L-pyroglutamic acid to 4-alkyl-substituted L-prolines. The synthesis of trans-4-cyclohexyl-L-proline Journal of Organic Chemistry. ,vol. 51, pp. 3140- 3143 ,(1986) , 10.1021/JO00366A011
Roger A. N. C. Crump, Ian Fleming, Christopher J. Urch, Conjugate addition of the phenyldimethylsilyl group to αβ-unsaturated carbonyl compounds using a silylzincate in place of the silylcuprate J. Chem. Soc., Perkin Trans. 1. pp. 701- 706 ,(1994) , 10.1039/P19940000701
SATOSHI OMURA, KEIICHI MATSUZAKI, TOMOKO FUJIMOTO, KAZUHITO KOSUGE, TOSHIO FURUYA, SHIGEO FUJITA, AKIRA NAKAGAWA, Structure of lactacystin, a new microbial metabolite which induces differentiation of neuroblastoma cells. The Journal of Antibiotics. ,vol. 44, pp. 117- 118 ,(1991) , 10.7164/ANTIBIOTICS.44.117
Norbert Krause, Substituent Effects and Complexation Phenomena in the Diastereoselective Protonation of Chiral Enolates Angewandte Chemie International Edition in English. ,vol. 33, pp. 1764- 1765 ,(1994) , 10.1002/ANIE.199417641