Approach to the synthesis of cladiell-11-ene-3,6,7-triol.
[reaction: see text] The synthesis of an advanced intermediate in the synthesis of the title compound has been achieved. Key steps include an Ireland-Claisen rearrangement to install the C7 tertiary alcohol stereocenter, an SN2' reaction of an alkoxymethyl Cu reagent, and a diastereoselective Re-catalyzed allylic alcohol transposition.
Hutchison
John M
JM
University of Arkansas, Fayetteville, Arkansas 72701, USA.
Lindsay
Harriet A
HA
Dormi
Silvana S
SS
Jones
Gavin D
GD
Vicic
David A
DA
McIntosh
Matthias C
MC
D001952:Bridged-Ring Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D003300:Copper / Q000737:chemistry; D003500:Cyclization; D004224:Diterpenes / Q000138:chemical synthesis* / Q000737:chemistry; D005663:Furans / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure
D001952:Bridged-Ring Compounds; D004224:Diterpenes; D005663:Furans; C430551:cladiell-11-ene-3,6,7-triol; D003300:Copper