Enantioselective synthesis of pladienolide B and truncated analogues as new anticancer agents.
作者： Vemula Praveen Kumar , Srivari Chandrasekhar
DOI: 10.1021/OL401458D
关键词:
摘要: An enantioselective synthesis of natural anticancer macrolide pladienolide B is described. The synthetic highlights include Sharpless asymmetric epoxidation, ring closing metathesis (RCM), Ireland–Claisen rearrangement, Shi and Pd-catalyzed Stille coupling as key steps. route also allowed the truncated analogues (41a–d) B.
acs.org
core.ac.uk 
sci-hub.se 参考文章(53)
HIDENORI NAKAJIMA, BUNJI SATO, TAKASHI FUJITA, SHIGEHIRO TAKASE, HIROSHI TERANO, MASAKUNI OKUHARA, New Antitumor Substances, FR901463, FR901464 and FR901465 The Journal of Antibiotics. ,vol. 49, pp. 1196- 1203 ,(1996) , 10.7164/ANTIBIOTICS.49.1196
Robert E. Ireland, Richard H. Mueller, Alvin K. Willard, The ester enolate Claisen rearrangement. Stereochemical control through stereoselective enolate formation Journal of the American Chemical Society. ,vol. 98, pp. 2868- 2877 ,(1976) , 10.1021/JA00426A033
RALPH H. LAMBALOT, DAVID E. CANE, Isolation and characterization of 10-deoxymethynolide produced by Streptomyces venezuelae. The Journal of Antibiotics. ,vol. 45, pp. 1981- 1982 ,(1992) , 10.7164/ANTIBIOTICS.45.1981
Alexander L. Mandel, Brian D. Jones, James J. La Clair, Michael D. Burkart, A synthetic entry to pladienolide B and FD-895 Bioorganic & Medicinal Chemistry Letters. ,vol. 17, pp. 5159- 5164 ,(2007) , 10.1016/J.BMCL.2007.06.094
Ryoji Noyori, Isao Kurimoto, Electrochemical glycosylation method Journal of Organic Chemistry. ,vol. 51, pp. 4320- 4322 ,(1986) , 10.1021/JO00372A050
William R. Roush, Thomas D. Bannister, Michael D. Wendt, Jill A. Jablonowski, Karl A. Scheidt, Studies on the Synthesis of Bafilomycin A1: Stereochemical Aspects of the Fragment Assembly Aldol Reaction for Construction of the C(13)−C(25) Segment The Journal of Organic Chemistry. ,vol. 67, pp. 4275- 4283 ,(2002) , 10.1021/JO016413F
Yoshihiko Kotake, Koji Sagane, Takashi Owa, Yuko Mimori-Kiyosue, Hajime Shimizu, Mai Uesugi, Yasushi Ishihama, Masao Iwata, Yoshiharu Mizui, Splicing factor SF3b as a target of the antitumor natural product pladienolide Nature Chemical Biology. ,vol. 3, pp. 570- 575 ,(2007) , 10.1038/NCHEMBIO.2007.16
Barbara G. Isaac, Stephen W. Ayer, Robert C. Elliott, Richard J. Stonard, Herboxidiene: a potent phytotoxic polyketide from Streptomyces sp. A7847 Journal of Organic Chemistry. ,vol. 57, pp. 7220- 7226 ,(1992) , 10.1021/JO00052A042
Clayton H. Heathcock, Peggy A. Radel, Total synthesis of a slightly unnatural product. Confirmation of the stereostructure of the archaebacterial C40 diol by synthesis of a stereoisomer Journal of Organic Chemistry. ,vol. 51, pp. 4322- 4323 ,(1986) , 10.1021/JO00372A051
Isao Shimizu, Kaoruko Hayashi, Masato Oshima, A short stereoselective synthesis of (−)-serricornin Tetrahedron Letters. ,vol. 31, pp. 4757- 4758 ,(1990) , 10.1016/S0040-4039(00)97725-6