220460-40-2Relevant academic research and scientific papers
Stereoselective Preparation of Enantiomerically Pure Annulated Carbohydrates Using Ring-Closing Metathesis
Holt, David J.,Barker, William D.,Jenkins, Paul R.,Panda, Jagannath,Ghosh, Subrata
, p. 482 - 493 (2007/10/03)
Ring-closing metathesis has been applied to a series of glucose derivatives to produce cyclopentene derivatives 5a and 5b, cyclohexene derivatives 8 and 9, cycloheptene 12, and cyclooctene 14. Spirocyclic dihydrofurans 19, 26a, and 26b, along with dihydropyran 22, were also produced. A range of fused oxepine derivatives 29a-c and one oxo-cyclononene 31 were also prepared. Cyclopentene 5b was subjected to a sequence of hydrogenation, NBS bromination, and treatment with powdered zinc to furnish the ring-expanded product 35. No such ring expansion occurred when the cyclohexaannulated compound 8 was treated with NBS followed by powdered zinc, leading to aldehyde 39. The spiro dihydrofuran derivative 19 was converted to the aldehyde 42 via the same reaction sequence used to fragment cyclopentene derivative 5b.
Ring-closing metathesis in carbohydrate annulation
Holt, David J.,Barker, William D.,Jenkins, Paul R.,Davies, David L.,Garratt, Shaun,Fawcett, John,Russell, David R.,Ghosh, Subtrata
, p. 3298 - 3300 (2007/10/03)
Even eight-membered rings (such as in 2) can be formed by ring-closing metathesis of glucose derivatives P such as 1. Enantiomerically pure tricyclic spiro compounds can also be prepared.
