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Synfacts 2016; 12(12): 1225
DOI: 10.1055/s-0036-1589447
DOI: 10.1055/s-0036-1589447
Synthesis of Natural Products and Potential Drugs
Total Synthesis of (+)-Ryanodol
Further Information
Publication History
Publication Date:
17 November 2016 (online)
Key words
(+)-ryanodol - (+)-anhydroryanodol - Pauson–Khand reaction - reductive cyclization - selenium dioxide oxidationSignificance
(+)-Ryanodol is a highly oxidized complex diterpenoid and the hydrolysis product of ryanodine. It modulates intracellular Ca2+ channels, albeit with lower affinity than the parent natural product. Reisman and co-workers completed the synthesis of (+)-ryanodol in only 15 steps from (S)-pulegone.
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Comment
Key intermediate G was assembled in seven steps from (S)-pulegone and transformed into enone H by a highly diastereoselective Pauson–Khand reaction. Treatment of tetracycle H with SeO2 under strictly anhydrous conditions led to the simultaneous installation of three oxygen functionalities. (+)-Anhydroryanodol was finally converted into (+)-ryanodol by epoxidation and reductive cyclization.
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