(+)-Phoslactomycin B was synthesized by a highly enantio- and stereoselective approach involving asymmetric pentenylation, Suzuki-Miyaura coupling, ring-closing metathesis, asymmetric dihydroxylation, and Stille coupling. The synthetic method developed enables us to synthesize three other isomers concerning the C11-OH and Delta12-double bond.

A general methodology applicable for the synthesis of the phoslactomycin family of antibiotics, potent and selective protein phosphatase inhibitors, has been developed starting from a beta-isocupreidine-catalyzed asymmetric Baylis-Hillman reaction of 3-(4-methoxybenzyloxy)propanal with hexafluoroisopropyl acrylate, and thereby formal syntheses of (+)-fostriecin and (+)-phoslactomycin B have been accomplished.

NW-G01, a cyclic hexapeptide antibiotic, and 34-epi-NW-G01 were synthesized by the highly stereoselective convergent approach for the first time, thereby unambiguously determining the absolute structure of NW-G01.

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Enantio-and Stereoselective Route to the Phoslactomycin Family of Antibiotics: Formal Synthesis of (+)-Fostriecin and (+)-Phoslactomycin B. -A general methodology applicable to the synthesis of the phoslactomycin family is developed. Key steps are the β-isocupreidine-catalyzed a symmetric Baylis-Hillman reaction of aldehyde (I) with acrylate (II). The following transformations afford the suitable precursors for metathesis reactions to construct the unsaturated lactone moiety, cf. formation of (V) and (XII). -(SARKAR, S. M.; WANZALA, E. N.; SHIBAHARA, S.; TAKAHASHI, K.; ISHIHARA, J.; HATAKEYAMA*, S.; Chem.