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  • Title: Total synthesis of pectenotoxin-2.
    Author: Fujiwara K, Suzuki Y, Koseki N, Aki Y, Kikuchi Y, Murata S, Yamamoto F, Kawamura M, Norikura T, Matsue H, Murai A, Katoono R, Kawai H, Suzuki T.
    Journal: Angew Chem Int Ed Engl; 2014 Jan 13; 53(3):780-4. PubMed ID: 24288200.
    Abstract:
    Pectenotoxin-2 (PTX2) is a shellfish toxin and has a non-anomeric spiroacetal, which is not stabilized by an anomeric effect. The selective construction of the non-anomeric spiroacetal has been a major problem in the synthesis of PTX2. Described herein is the stereoselective total synthesis of PTX2 via the isomerization of anomeric spiroacetal pectenotoxin-2b (PTX2b). The synthesis of PTX2b was achieved by a simple process including sulfone-mediated assembly of spirocyclic and bicyclic acetals and subsequent macrocyclization by ring-closing olefin metathesis. Finally, the selective construction of PTX2 was accomplished by the early termination of a dynamic transition process to equilibrium in the acid-catalyzed isomerization of anomeric PTX2b. [6,6]-Spiroacetal pectenotoxin-2c (PTX2c) was also synthesized from PTX2b. The cytotoxicity assay of the synthetic compounds against HepG2 and Caco2 cancer cells showed a potency of the order: PTX2≫PTX2b>PTX2c.
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