Natural
Products

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

Abstract: 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.

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.

Tung, James C.; Chen, Wensheng; Noll, Bruce C.; Taylor, Richard E.; Fields, Stephen C.; Dent, William H., III; Green, F. Richard, III. "Towards the Synthesis of the Cornexistins", Synthesis 2007, 15, 2388.

Abstract:  A concise synthetic route to the carbocyclic core I of the cornexistins is reported. The route is highlighted by a Diels-Alder cycloaddn./oxidative cleavage strategy to generate the central highly functionalized nine-member ring. A silyl-tethered ring-closing metathesis strategy is utilized to control trisubstituted alkene geometry.

Schmitzer, Paul R.; Graupner, Paul R.; Chapin, Eleanor L.; Fields, Steven C.; Gilbert, Jeff R.; Gray, Jim A.; Peacock, Cathy L.; Gerwick, B. Clifford "Ribofuranosyl Triazolone: A Natural Product Herbicide with Activity on Adenylosuccinate Synthetase Following Phosphorylation", J. Nat. Prod. 2000, 63, 777.

Abstract:  2,4-Dihydro-4-(β-D-ribofuranosyl)-1,2,4(3H)-triazol-3-one (I) was identified as the principal phytotoxic component of a fermn. broth derived from an Actinomadura. I was also synthesized. Metabolite reversal studies suggested the target site was adenylosuccinate synthetase, which was confirmed by direct measurement of the activity of the 5'-phosphorylated deriv. on the isolated enzyme.