Spongistatine, Cynachyrolide oder Altohyrtine? Marine Makrolide in der Krebsforschung

The spongipyrans comprise an important family of architecturally unique bis-spiroketal macrolides that display extraordinary (subnanomolar) antitumor activities against a wide variety of human cancer cell lines, including melanoma, lung, colon, and brain. [1] Three research groups (those of Pettit, [1a, 2] Fusetani, [3] and Kitagawa [4] ) independently isolated members of the spongipyran family in minute amounts, naming them in turn the spongistatins, cinachyrolide, and the altohyrtins. [5] Whereas the carbon skeleton was common to all three families, the structures differed in the assignment of the relative stereochemical relationships. Kitagawa and coworkers assigned the correct relative and absolute stereochemistries based on extensive Mosher analysis and circular dichroism studies. [4c] These assignments were subsequently confirmed by the total syntheses of ()-altohyrtin C [spongistatin 2 (2)] by Evans et al. [6] and ()-altohyrtin A [spongistatin 1(1)] by Kishi and co-workers. [7] The elegant syntheses at Harvard University demonstrated unequivocally that the altohyrtins and spongistatins were indeed identical.The spongistatins have attracted wide interest [8] as a result of their architectural complexity, which includes two [6,6] spiroketal moieties, [9] two highly substituted tetrahydropyran rings encased in a 42 membered macrolide framework, 24 stereogenic centers, and a delicate triene side chain. Particularly intriguing is the CD spiroketal possessing only a single anomeric interaction in conjunction with an intramolecular hydrogen bond that stabilizes the axial ± equatorial configuration.To assemble the complex spongipyran skeleton, we envisioned Wittig union of 5 with 6 (Scheme 1), followed by regioselective macrolactonization at C(41), first demonstrated

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Stereocontrolled Total Synthesis of (+)‐Altohyrtin A/Spongistatin 1

Paterson¹,

Chen²,

Coster³

et al. 2001

Angewandte Chemie

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Spongistatine, Cynachyrolide oder Altohyrtine? Marine Makrolide in der Krebsforschung

Cited by 8 publications

References 38 publications

Stereodivergent Synthesis of Highly Substituted Tetrahydropyrans

Stereodivergent Synthesis of Highly Substituted Tetrahydropyrans

The Spongistatins: Architecturally Complex Natural Products—Part One: A Formal Synthesis of (+)-Spongistatin 1 by Construction of an Advanced ABCD Fragment

Stereocontrolled Total Synthesis of (+)‐Altohyrtin A/Spongistatin 1

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