Desymmetrization of cyclic anhydrides using dihydroxy compounds: selective synthesis of macrocyclic tetralactones

Organic Letters
Sengodagounder MuthusamyEringathodi Suresh

Abstract

[reaction: see text] The desymmetrization of cyclic anhydrides is carried out using dihydroxy compounds. A mild route to synthesize fused saturated/unsaturated macrocyclic tetralactones with different ring sizes (20-34) having a wide variety of spacers is described. The structure is confirmed by the representative single-crystal X-ray analysis. The multiple reduction of unsaturated macrocyclic tetralactones is also illustrated. This method is mild, selective, and efficient and achieves high yield.

References

Sep 1, 1977·Angewandte Chemie·S MasamuneJ W Corcoran
Aug 14, 2003·Chemical Reviews·Yonggang ChenLi Deng
Sep 27, 2003·The Journal of Organic Chemistry·Zhiguo ZhouStephen R Wilson
Jun 19, 2004·The Journal of Organic Chemistry·Shunya TakahashiTadashi Nakata
Jun 17, 2005·Organic Letters·Omid Soltani, Jef K De Brabander

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Citations

Jan 27, 2007·The Journal of Organic Chemistry·Sengodagounder MuthusamyEringathodi Suresh

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