Total Synthesis of (+)-Rubriflordilactone A.
Two enantioselective total syntheses of the nortriterpenoid natural product rubriflordilactone A are described, which use palladium- or cobalt-catalyzed cyclizations to form the CDE rings, and converge on a late-stage synthetic intermediate. These key processes are set up through the convergent coupling of a common diyne component with appropriate AB-ring aldehydes, a strategy that sets the stage for the synthetic exploration of other members of this family of natural products.
Chemistry Research Laboratory, University of Oxford, 12 Mansfield Road, Oxford, OX1 3TA (UK).
Shermin S
SS
Goh
Chemistry Research Laboratory, University of Oxford, 12 Mansfield Road, Oxford, OX1 3TA (UK).
Guilhem
G
Chaubet
Chemistry Research Laboratory, University of Oxford, 12 Mansfield Road, Oxford, OX1 3TA (UK).
Birgit
B
Gockel
Chemistry Research Laboratory, University of Oxford, 12 Mansfield Road, Oxford, OX1 3TA (UK).
Marie-Caroline A
MC
Cordonnier
Institute of Organic Chemistry, RWTH Aachen University, Landoltweg 1, 52074 Aachen (Germany).
Hannah
H
Baars
Chemistry Research Laboratory, University of Oxford, 12 Mansfield Road, Oxford, OX1 3TA (UK).
Andrew W
AW
Phillips
Chemistry Research Laboratory, University of Oxford, 12 Mansfield Road, Oxford, OX1 3TA (UK). edward.anderson@chem.ox.ac.uk.
Edward A
EA
Anderson
D001688:Biological Products / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D003035:Cobalt / Q000737:chemistry; D003500:Cyclization; D032135:Kadsura / Q000737:chemistry; D010165:Palladium / Q000737:chemistry; D032141:Schisandra / Q000737:chemistry; D013237:Stereoisomerism; D014315:Triterpenes / Q000138:chemical synthesis* / Q000737:chemistry
D001688:Biological Products; D014315:Triterpenes; C514794:rubriflordilactone A; D003035:Cobalt; D010165:Palladium
cyclotrimerization; domino reactions; natural products; total synthesis; transition metal catalysis