Total Syntheses of Rhodiolosides A and D and of Sachalinols A–C | Zendy

Simon Kristina | Zendy; Jones Peter G. | Zendy; Lindel Thomas | Zendy

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Total Syntheses of Rhodiolosides A and D and of Sachalinols A–C

Author(s) -

Simon Kristina,

Jones Peter G.,

Lindel Thomas

Publication year - 2011

Publication title -

european journal of organic chemistry

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.825

H-Index - 155

eISSN - 1099-0690

pISSN - 1434-193X

DOI - 10.1002/ejoc.201001315

Subject(s) - chemistry , geraniol , tetrahydrofuran , bromide , organic chemistry , derivative (finance) , stereochemistry , absolute configuration , chromatography , essential oil , financial economics , economics , solvent

The glucosylated monoterpenoids (–)‐rhodioloside A and (–)‐rhodioloside D from the roseroot ( Rhodiola rosea ) have been synthesized for the first time. Glucosylation with tetrapivaloylglucosyl bromide proved superior to the use of tetraacetylglucosyl bromide or glucosyl iodides. Acid‐catalyzed cyclization of a homoglycidol‐type geraniol derivative afforded the monoterpenoid tetrahydrofuran (+)‐sachalinol C from Rhodiola sachalinensis . The absolute configuration of (+)‐sachalinol C requires revision. (–)‐Sachalinol A and (–)‐sachalinol B were also obtained.

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