title: Total synthesis of myceliothermophins C, D, and E.
abstract: The total synthesis of cytotoxic polyketides myceliothermophins E (1), C (2), and D (3) through a cascade-based cyclization to form the trans-fused decalin system is described. The convergent synthesis delivered all three natural products through late-stage divergence and facilitated unambiguous C21 structural assignments for 2 and 3 through X-ray crystallographic analysis, which revealed an interesting dimeric structure between its enantiomeric forms.
authors.affiliation: Department of Chemistry, BioScience Research Collaborative, Rice University, 6100 Main Street, Houston, TX 77005 (USA). kcn@rice.edu.
authors.forename: K C
authors.initials: KC
authors.lastname: Nicolaou
authors.forename: Lei
authors.initials: L
authors.lastname: Shi
authors.forename: Min
authors.initials: M
authors.lastname: Lu
authors.forename: Manas R
authors.initials: MR
authors.lastname: Pattanayak
authors.forename: Akshay A
authors.initials: AA
authors.lastname: Shah
authors.forename: Heraklidia A
authors.initials: HA
authors.lastname: Ioannidou
authors.forename: Manjunath
authors.initials: M
authors.lastname: Lamani
mesh_terms: D001688:Biological Products / Q000138:chemical synthesis* / Q000737:chemistry; D018360:Crystallography, X-Ray; D003500:Cyclization; D008968:Molecular Conformation; D009281:Naphthalenes / Q000737:chemistry; D009579:Nitrobenzoates / Q000737:chemistry; D061065:Polyketides / Q000138:chemical synthesis* / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D001688:Biological Products; D009281:Naphthalenes; D009579:Nitrobenzoates; D061065:Polyketides; C000598017:myceliothermophin C; C000598018:myceliothermophin D; C000598016:myceliothermophin E; C007229:decalin
keywords: cascade reactions; decalin; natural products; polyketides; total synthesis