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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
Abstract 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.