A Biomimetic Stereoselective Approach to Euolutchuol C and Its Structural Assignment

The first stereoselective total synthesis of euolutchuol C using a biomimetic cationic polyene cyclization is demonstrated, and its absolute structure has been established. Four potential stereoisomers of euolutchuol C were synthesized to confirm the structure as an aromatic abietane diterpenoid con...

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Veröffentlicht in:European journal of organic chemistry 2023-11, Vol.26 (43)
Hauptverfasser: R. S., Reyno, Surendran, Sravya, James, Glory, Rajendar, Goreti
Format: Artikel
Sprache:eng
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Zusammenfassung:The first stereoselective total synthesis of euolutchuol C using a biomimetic cationic polyene cyclization is demonstrated, and its absolute structure has been established. Four potential stereoisomers of euolutchuol C were synthesized to confirm the structure as an aromatic abietane diterpenoid consisting of 15( S )‐stereogenic center. Asymmetric Sharpless dihydroxylation was employed to construct the chiral epoxide, while CBS‐reduction was utilized for enantiomerically pure benzylic alcohols. A convergent approach is used to synthesize euolutchuol C in seven longest linear steps to give an overall yield of 23 %.
ISSN:1434-193X
1099-0690
DOI:10.1002/ejoc.202300748