99440-69-4

Upstream product

• 51716-32-6 ethyl 4-oxo-1,2,3-trimethyl-2-cyclohexene-1-carboxylate 
• 609-14-3 2-acetylpropanoic acid ethyl ester 
• 99440-45-6 4-hydroxy-2-methyl-3-oxo-2-(3-oxopentyl)butanoic acid γ-lactone 
• 94884-73-8 4,8-dimethyl-1,5-dioxo-2-oxabicyclo<4.3.0>non-4(9)-ene 
• 1629-58-9 4-penten-3-one 
• 1192-51-4 3-methyl-furan-2,4-dione 

Relevant academic research and scientific papers

Studies culminating in the total synthesis and determination of the absolute configuration of (-)-saudin

A full account of studies that culminated in the total synthesis of both antipodes and the assignment of its absolute configuration of Saudin, a hypoglycemic natural product. Two approaches are described, the first proceeding though bicyclic lactone intermediates and related second monocyclic esters. The former was obtained via asymmetric Diels-Alder cycloaddition and the latter by an asymmetric annulation protocol. Both approaches employ a Lewis acid promoted Claisen rearrangement, with the successful approach taking advantage of bidentate chelation to control the facial selectivity of the key Claisen rearrangement.

Stereoselective Synthesis of Trisporic Acids A and B, Their Methyl Esters, and Trisporols A and B, Hormones and Prohormones of Mucoraceous Fungi

Syntheses of (9E)- and (9Z)-trisporic acids A (1 and 4) and B (2 and 5) and the corresponding methyl esters (7, 10, 8, and 11, respectively) were accomplished via the Wittig reaction of lactol 52 with an appropriate phosphorane.The lactol was prepared by