Fluorous mixture synthesis of (-)-dictyostatin and three stereoisomers
- PMID: 16408900
- DOI: 10.1021/ol0526827
Fluorous mixture synthesis of (-)-dictyostatin and three stereoisomers
Abstract
[reaction: see text] A mixture of four stereoisomers whose configurations are encoded by fluorous silyl protecting groups has been prepared and converted over 22 steps to a mixture of protected dictyostatins. Demixing by fluorous HPLC followed by removal of the fluorous protecting groups (detagging) provides dictyostatin and three C6,C7 stereoisomers. Biological evaluation showed that the monoepimers of the natural product retained highly potent activity.
Similar articles
-
Structure assignment of lagunapyrone B by fluorous mixture synthesis of four candidate stereoisomers.J Am Chem Soc. 2006 Nov 1;128(43):14200-5. doi: 10.1021/ja064812s. J Am Chem Soc. 2006. PMID: 17061905
-
Synthesis of all 16 stereoisomers of pinesaw fly sex pheromones--tools and tactics for solving problems in fluorous mixture synthesis.J Org Chem. 2005 Nov 11;70(23):9447-62. doi: 10.1021/jo051526a. J Org Chem. 2005. PMID: 16268620
-
Synthesis and biological evaluation of (-)-16-normethyldictyostatin: a potent analogue of (-)-dictyostatin.Org Lett. 2005 Jul 7;7(14):2873-6. doi: 10.1021/ol050808u. Org Lett. 2005. PMID: 15987158
-
Gamma-fluorinated analogues of glutamic acid and glutamine.Amino Acids. 2003 Apr;24(3):245-61. doi: 10.1007/s00726-002-0410-9. Amino Acids. 2003. PMID: 12707806 Review.
-
Development of practical syntheses of the marine anticancer agents discodermolide and dictyostatin.Nat Prod Rep. 2008 Apr;25(2):342-75. doi: 10.1039/b705661n. Epub 2008 Feb 27. Nat Prod Rep. 2008. PMID: 18389141 Review.
Cited by
-
Vinylogous aldol products from chiral crotylsilanes obtained by enantioselective Rh(II) and Cu(I) carbenoid Si-H insertion.Org Lett. 2010 May 7;12(9):2112-5. doi: 10.1021/ol100604m. Org Lett. 2010. PMID: 20387893 Free PMC article.
-
Synthetic applications of fluorous solid-phase extraction (F-SPE).Tetrahedron. 2006 Dec 18;62(51):11837-11865. doi: 10.1016/j.tet.2006.08.051. Tetrahedron. 2006. PMID: 18509513 Free PMC article. No abstract available.
-
Synthesis and biological evaluation of (-)-dictyostatin and stereoisomers.Tetrahedron. 2007 Aug 27;63(35):8537-8562. doi: 10.1016/j.tet.2007.05.033. Tetrahedron. 2007. PMID: 18728696 Free PMC article.
-
A "shortcut" Mosher ester method to assign configurations of stereocenters in nearly symmetric environments. Fluorous mixture synthesis and structure assignment of petrocortyne A.J Am Chem Soc. 2009 Apr 22;131(15):5411-3. doi: 10.1021/ja900849f. J Am Chem Soc. 2009. PMID: 19323551 Free PMC article.
-
Conformation-activity relationships of polyketide natural products.Nat Prod Rep. 2015 Aug;32(8):1183-206. doi: 10.1039/c5np00014a. Nat Prod Rep. 2015. PMID: 25974024 Free PMC article. Review.
Publication types
MeSH terms
Substances
Grants and funding
LinkOut - more resources
Full Text Sources
Miscellaneous