title: Ready access to functionally embellished cis-hydrindanes and cis-decalins: protecting group-free total syntheses of (±)-Nootkatone and (±)-Noreremophilane.
abstract: A simple and efficient synthesis of functionalized cis-hydrindanes and cis-decalins was achieved using a sequential Diels-Alder/aldol approach in a highly diastereoselective manner. The scope of this method was tested with a variety of substrates and was successfully applied to the synthesis of two natural products in racemic form. The highlights of the present work provide ready access to 13 new cis-hydrindanes/cis-decalins, a protecting group-free total synthesis of an insect repellent Nootkatone, and the first synthesis of a Noreremophilane using the shortest sequence.
authors.affiliation: CSIR-National Chemical Laboratory, Dr. Homi Bhabha Road, Pune, 411008, India.
authors.forename: Kishor L
authors.initials: KL
authors.lastname: Handore
authors.forename: B
authors.initials: B
authors.lastname: Seetharamsingh
authors.forename: D Srinivasa
authors.initials: DS
authors.lastname: Reddy
mesh_terms: D007189:Indans / Q000737:chemistry*; D015394:Molecular Structure; D009281:Naphthalenes / Q000737:chemistry*; D000081223:Polycyclic Sesquiterpenes; D012717:Sesquiterpenes / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D007189:Indans; D009281:Naphthalenes; D000081223:Polycyclic Sesquiterpenes; D012717:Sesquiterpenes; C531997:hydrindane; C584911:noreremophilane; C007229:decalin; C050302:nootkatone