Meyers total synthesis

Numerous applications of the Ni(n)/Cr(ii)-mediated coupling reaction in total synthesis have already been reported.11 Some of the more noteworthy examples derive from Kishi s laboratories and played a role in the syntheses of such complex molecules as (+)-ophiobolin C16 and halichondrin B17 (see Scheme 5). Another elegant application can be found in the enantioselective total syntheses of (+)-brefeldin C and 4-ep/-brefeldin C by Schreiber and Meyers (see Scheme 5).18... 

Another example of macrocyclic RCM with a diene-ene was disclosed in 2000 by Meyers and coworkers in the first total synthesis of griseoviridin (223) [ 107]. Griseoviridin is a highly complex member of the family of streptogramin antibiotics, featuring a 23-membered unsaturated bis-lactam core incorporat-... 

There has been no report on this kind of compound in the literature for the period concerned. The perhydro derivatives were, on the contrary, well-studied for several years and applied in a variety of routes for the total synthesis of natural products or to produce optically active derivatives, mainly following the Meyers protocol <1984JA1146>. Only two examples of dihydropyrrolo[2,l- ]oxazoles are available and one example of a tetrahydro derivative is described. 

The potential of this sequence was applied in Meyers s total synthesis of antibiotic maytansinoids such as (-)-maysine [345]. 

Romo D, Meyer SD et al (2002) Total synthesis of (—)-rapamycin using an Evans-Tish-chenko fragment coupling. J Am Chem Soc 115 7906-7907... 

The first total synthesis of camosic acid (89). was accomplished by Meyer et al. [28], Meyer developed two different routes for the synthesis of camosic acid. This is exhibited in Figs. (12) and (13). 

Meyers, A. I., Miller, D. B and White, K H Chiral and achiral formamidine in synthesis. The first asymmetric route to (—)-yohirabone and an efficient total synthesis of ( )-yohim-bone, J. Am. Chem Soc., 110,4778, 1988. 

Oxidation. Meyers et aV used Saigo s reagent (1) for oxidation of the primary alcohol 2 to 3 (70.5% yield). The reaction was one step in the total synthesis of maysine (4). 

Recently, Meyers and Hutchings employed the entrainment of magnesium as a key step in the total synthesis of oxoassoanine as shown in Scheme 1 [20]. 

In the laboratory of A.I. Meyers, the first enantioselective total synthesis of the streptogramin antibiotic (-)-madumycin II was achieved. The natural product contains an oxazole moiety, which may be considered a masked dehydropeptide. The oxazole moiety was introduced in two steps by the Burgess cyciodehydration reaction followed by oxidation of the resulting oxazoline to the corresponding oxazole. 

In the laboratory of S.C. Welch, the Meyer-Schuster rearrangement was the key step in the stereoselective total synthesis of the antifungal mold metabolite (+)-LL-Z1271a. A tricyclic enone acetal was treated with lithium ethoxyacetylide, and the crude product was exposed to H2SO4 in anhydrous methanol, which brought about the rearrangement and afforded the desired product in 30% yield along with 12% of an epimer. 

An intramolecular variant of the Stork enamine synthesis was utilized during the asymmetric total synthesis of (-)-8-aza-12-oxo-17-desoxoestrone by A.I. Meyers et al. ... 

Meyer, J.H., and Bartlett, P.A., Macrocyclic inhibitors of penicillopepsin. Part 1. Design, synthesis, and evaluation of an inhibitor bridged between Pl and P3, J. Am. Chem. Soc., 120, 4600, 1998. Noguchi, H., Aoyama, T., and Shioiri, T., Total synthesis of analogs of topostin B, a DNA topoi-somerase 1 inhibitor. Part 1. Synthesis of fragments of topostin B-1 analogs. Tetrahedron, 51, 10531, 1995. 

H. Rink, M. Liersch, P. Sieber, and F. Meyer. A large fragment approach to DNA synthesis total synthesis of a gene for the protease inhibitor eglin c from leech Hirudo medicinalis and its expression in E. coli. Nucl. Acids Res. 72 6369 (1984). 

Meyers has shown that during the total synthesis of (-)-bistatramide C, the valine-serine derived dipeptide 31, when exposed to 1, forms the expected oxazoline 33 analog along with the elimination compound 32. 33 was further converted to the oxazole 34 with use of NiC>2 or MnC>2.8... 

Williams, D. R., and Meyer, K. G. (1999). Total synthesis of (+)-amphidinolide K. In Abstracts of Papers, 218th National Meeting of the American Chemical Society, 1999, p. 578-ORGN. American Chemical Society, Washington, DC. 

To date, only three research groups have communicated syntheses of isoschizandrin. The Meyers groupfirst reported the total synthesis of (-)-isoschizandrin, thereby establishing the absolute stereochemistry of the natural product. This was soon followed by a racemic synthesis of ( )-isoschizandrin from the laboratories of Tobinaga. More recently, Tanaka and coworkers reported the first asymmetric total synthesis of (+)-isoschizandrin. ... 

Simultaneously, Meyers and co-workers" described the first total synthesis of (—)-madumycin II 1183. They envisioned construction of 1183 from the oxazole-dienylamine 1203 and the D-alanyl ester 1252 (Scheme 1.319). 

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