Stereochemical Assignment of the C1−C6 Fragment of Psymberin by Synthesis and Natural Product Degradation
- 18 August 2005
- journal article
- letter
- Published by American Chemical Society (ACS) in Organic Letters
- Vol. 7 (19) , 4117-4120
- https://doi.org/10.1021/ol051396s
Abstract
[reaction: see text] Psymberin is a sponge-derived natural product that shows striking selectivity as a cytotoxic agent. Conformational mobility has precluded stereochemical assignment for the acyl fragment of this molecule (psymberic acid) by NMR. Herein we report stereoselective syntheses of all four stereoisomers of psymberic acid. A comparison of the acid-mediated cyclization products of these compounds to the product of psymberin's acidic methanolysis showed the stereochemical configuration of this fragment to be 4S,5S.Keywords
This publication has 10 references indexed in Scilit:
- Configuration of the Psymberin Amide Side ChainOrganic Letters, 2005
- Psymberin, A Potent Sponge-Derived Cytotoxin from Psammocinia Distantly Related to the Pederin FamilyOrganic Letters, 2004
- Highly Selective Hydrolytic Kinetic Resolution of Terminal Epoxides Catalyzed by Chiral (salen)CoIIIComplexes. Practical Synthesis of Enantioenriched Terminal Epoxides and 1,2-DiolsJournal of the American Chemical Society, 2002
- Asymmetric Total Synthesis of Taxol\RChemistry – A European Journal, 1998
- Stereocontrolled synthesis of C10-C22 fragment of the immunosuppressant FK 506. An occurrence of complementary stereoselectivity in the C15 ketone reductionTetrahedron: Asymmetry, 1996
- Bioactive marine metabolites. 41. Theopederins A-E, potent antitumor metabolites from a marine sponge, Theonella spThe Journal of Organic Chemistry, 1992
- Antiviral and antitumor agents from a New Zealand sponge, Mycale sp. 2. Structures and solution conformations of mycalamides A and BThe Journal of Organic Chemistry, 1990
- Isolation and structure elucidation of onnamide A, a new bioactive metabolite of a marine sponge, Theonella spJournal of the American Chemical Society, 1988
- Mycalamide A, an antiviral compound from a New Zealand sponge of the genus MycaleJournal of the American Chemical Society, 1988
- Chelation- and non-chelation-controlled additions to 2-O-benzyl-3-O-(tert-butyldimethylsilyl)glyceraldehydeThe Journal of Organic Chemistry, 1985