Organophosphorus

Fields, S. C. "Synthesis of Natural Products Containing a C-P Bond" Tetrahedron 1999, 55, 12237.

Abstract:  The authors present a review with 159 refs. on the synthesis of natural products contg. a C-P bond.

Fields, S. C. "Total Synthesis of the Natural Product Phosphonothrixin". Tetrahedron Lett., 1998, 39, 6621.

Abstract: Synthesis of the novel natural product phosphonothrixin, MeCOC(OH)(CH2OH)CH2P(:O)(OH)2, has been accomplished in 6 steps and 24% overall yield from the com. available Baylis-Hillman adduct, MeCH(OH)C(:CH2)CO2Me, derived from acetaldehyde and Me vinyl ketone. The synthesis features use of a trisubstituted olefin as a latent a-hydroxyketone, which formally reverses the oxidn. states of the hydroxyl and carbonyl functionalities. This alleviates some of the difficulties encountered in alternative syntheses which proceed through metastable intermediates.

W. H. Dent III, S. C. Fields, Paul R. Graupner, E. G. Tromiczak" "9-BBN-Protected Amino Acids and Their Use in Natural Product Synthesis. Part I. Total Synthesis of Octicidin." Poster Presentation at CU-Roche/Syntex Symposium May 22, 1996, Boulder, CO.

Abstract:  The natural product octicidin is the only known molecule to boast a 5 heteroatom linkage with the exception of pyrophosphate. It's unique structure contains a highly unstable sulfonated phosphotriamide. This natural product was synthesized in 4 steps and its herbicidal activity confirmed.