Synthesis of the non-adjacent bis-THF core of cis-sylvaticin using a double oxidative cyclisation.
A short synthesis of the non-adjacent bis-THF core of the Annonaceous acetogenin cis-sylvaticin (1) is described. C(2) Symmetrical (Z,E,E,Z)- and (E,E,E,E)-tetraenes and were synthesised in six and three steps respectively from (1E,5E,9E)-cyclododeca-1,5,9-triene. Subsequent permanganate promoted asymmetric bi-directional oxidative cyclisation of tetraene was used to create the non-adjacent bis-THF core of 1, installing seven of the nine stereogenic centres present in the natural product in a single step. Desymmetrization of the oxidative cyclisation product by mono-tosylation gave access to a C11-C32 fragment of cis-sylvaticin.
Bhunnoo
Riaz A
RA
The School of Chemistry, University of Southampton, Highfield, Southampton SO171BJ, UK.
Hobbs
Heather
H
Lainé
Dramane I
DI
Light
Mark E
ME
Brown
Richard C D
RC
D003500:Cyclization; D005663:Furans / Q000138:chemical synthesis / Q000737:chemistry*; D010084:Oxidation-Reduction; D011090:Polyenes / Q000737:chemistry; D013237:Stereoisomerism
D005663:Furans; D011090:Polyenes; C063434:sylvaticin