title: An approach to a bislactone skeleton: a scalable total synthesis of (±)-penifulvin A.
abstract: An efficient and scalable total synthesis of the architecturally challenging sesquiterpenoid (±)-penifulvin A has been accomplished via a 12-step sequence with an overall yield of 16%. For the construction of this structurally complex tetracyclic molecule, the key steps used included 1,4-conjugate addition, a Pd(0) catalyzed cross-coupling reaction between an enol phosphate and trimethyl aluminum, Claisen rearrangement using the Johnson orthoester protocol, Ti(III)-mediated reductive epoxide opening-cyclization, Lewis acid catalyzed epoxy-aldehyde rearrangement, and finally a substrate controlled oxidative cascade lactonization process.
authors.affiliation: CSIR-Central Drug Research Institute , Sector 10, Jankipuram Extension, Sitapur Road, Lucknow 226031, India.
authors.forename: Dipendu
authors.initials: D
authors.lastname: Das
authors.forename: Ruchir
authors.initials: R
authors.lastname: Kant
authors.forename: Tushar Kanti
authors.initials: TK
authors.lastname: Chakraborty
mesh_terms: D003500:Cyclization; D004852:Epoxy Compounds; D058116:Lewis Acids / Q000737:chemistry; D015394:Molecular Structure; D010084:Oxidation-Reduction; D010407:Penicillium / Q000737:chemistry; D012717:Sesquiterpenes / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism; D014025:Titanium / Q000737:chemistry
chemical_list: D004852:Epoxy Compounds; D058116:Lewis Acids; D012717:Sesquiterpenes; C515096:penifulvin A; D014025:Titanium