Enantiospecific first total synthesis and assignment of absolute configuration of the sesquiterpene (-)-cucumin H.
The first total synthesis of the sesquiterpene (-)-cucumin H, a linear triquinane isolated from Macrocystidia cucumis, has been accomplished starting from (R)-limonene employing two different cyclopentannulation methodologies, which in addition to confirming the structure also established the absolute configuration of the natural product. [reaction: see text]
Srikrishna
A
A
Department of Organic Chemistry, Indian Institute of Science, Bangalore 560012, India. ask@orgchem.iisc.ernet.in
Dethe
Dattatraya H
DH
D018360:Crystallography, X-Ray; D003517:Cyclopentanes / Q000737:chemistry; D008968:Molecular Conformation; D009579:Nitrobenzoates / Q000737:chemistry; D010084:Oxidation-Reduction; D012717:Sesquiterpenes / Q000138:chemical synthesis* / Q000737:chemistry*; D013237:Stereoisomerism; D013729:Terpenes / Q000737:chemistry
D003517:Cyclopentanes; D009579:Nitrobenzoates; D012717:Sesquiterpenes; D013729:Terpenes; C478875:cucumin H