Synthesis pectenotoxin

Awakiwa, D., Fujiwara, K., and Miwai, A. 2000. Syndietic studies on pectenotoxins synthesis of the common C8-C18 THF fragment. Synlett 1733—1736. 

Evans, D.A., Rajapakse, H.A., and Stenkamp, D. 2002. Asymmetric syntheses of pectenotoxins-4 and -8, part I synthesis of the C1-C19 subunit. Angew Chem IntEdEngl 41, 4569-4573. 

Fujiwara, K., Kobayashi, M., Yamamoto, E, Aki, Y.-L, Kawamura, M., Awakura, D., Amano, S., Okano, A., Murai, A., Kawai, H., and Suzuki, T. 2005. Synthesis of the common left-half part of pectenotoxins. Tetrahedron Lett 46, 5067-5069. 

Micalizio, G.C., and Roush, W.R. 2001. Studies on file synthesis of pectenotoxin II synthesis of a C(Zingone et al. 2006)-C(Pavela-Vrancic et al. 2001) fragment precursor via [3 + 2]-annulation reactions of chiral allylsilanes. OrgLett 3,1949-1952. 

Very recently, Donohoe et al. [11] used a similar domino process in the efficient synthesis of the ABC spiroacetal 23 ring system of pectenotoxin-4 24. In this reaction, triol 21 was converted into the bis-THF compound 22 with a yield of 69% using potassium osmate in an aqueous acetonitrile solution with pyridine-N-oxide (PNO) as a re-oxidant and a Lewis acid as promoter. The resulting compound 22... 

Vellucci D, Rychnovsky SD. Diastereoselective synthesis of the pectenotoxin 2 non-anomeric AB sprroacetal. Org. Lett. 2007 9 711 714. 

HaMm, R., Brimble, M.A., and Merten, J. (2006) Synthesis of the ABC tricyclic fragment of the pectenotoxins via stereocontrolled cydization of a y-hydroxyepoxide appended to the AB spiroacetal unit. Org. Biomol. Chem., 4,1387-1399. 

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