Studies in sesquiterpenes—XXX : Synthesis of ar-himachalene and himachalanes

  title={Studies in sesquiterpenes—XXX : Synthesis of ar-himachalene and himachalanes},
  author={R. C. Pandey and S. Dev},
Abstract The conversion of β-himachalene into ar-himachalene by a “low-temperature” -dehydrogenation-isomerization sequence is described and the unambiguous synthesis of ar-himachalene and himachalanes reported. 
Studies in sesquiterpenes—LI : β-Himachalene epoxide—stereochemistry and solvolysis
Stereochemistry of β-himachalene oxide has been established by its correlation with himachalol. Products of solvolysis of this oxide are dependent on conditions and reagents used. HomoallylicExpand
Studies in sesquiterpenes—XLVII : Cis- and trans-atlantones from Cedrus deodara loud☆☆☆
Isolation and characterisation of pure atlantone is reported for the first time, and has been found to have trans-geometry. A minor constituent of the essential oil from Cedrus deodara Loud is shownExpand
Studies in sesquiterpenes—LVIII : Deodardione, a sesquiterpene diosphenol and, limonenecarboxylic acid, a possible norsesquiterpene—compounds from the wood of cedrus deodara loud.
Isolation and structure elucidation of a C11 mono-carboxylic acid, apparently a nor-sesquiterpene, and, a sesquiterpene diosphenol from the essential oil of Cedrus deodara Loud. are described.
Studies in sesquiterpenes—LII: Isohimachalone: a constituent of the essential oil from wood of Cedrus deodara loud
Isolation and structure elucidation of a new bicyclic sesquiterpene of a new carbo-skeleton, from the essential oil from the wood of Credrus deodara loud., is reported. The structure rests on aExpand
Studies in sesquiterpenes—LIV : Oxidohimachalene, a novel sesquiterpenoid from the wood of Cedrus deodara loud
Abstract Isolation and structure elucidation of oxidohimachalene, a minor constituent of the essential oil of Cedrus deodara Loud., is described. A biomimetic-type conversion of β-himachalene intoExpand
Molecular rearrangement of epoxide derived from sesquiterpenes by Lewis acid catalysis
The molecular rearrangement under mild conditions of two epoxides derived from the sesquiterpenic himachalenes has been studied using BF 3 ·Et 2 O as the Lewis acid catalyst. Both reactions areExpand
Enantioselective synthesis of the essential oil and pheromonal component ar-himachalene by a chiral pool and chirality induction approach
Abstract The enantioselective synthesis of both isomers of ar -himachalene has been achieved starting from enantiomerically pure citronellal and p -methyl α-methyl styrene as an application of aExpand
Synthesis of (R)-ar-turmerone and its conversion to (R)-ar-himachalene, a pheromone component of the flea beetle: (R)-ar-himachalene is dextrorotatory in hexane, while levorotatory in chloroform
(R)-ar-Turmerone was synthesized from (4-methylphenyl)acetic acid by employing Evans asymmetric alkylation as the key step. (R)-ar-Turmerone was converted to (R)-ar-himachalene, which wasExpand
Lewis acid- and Bronsted acid-catalyzed stereoselective rearrangement of epoxides derived from himachalenes: access to new chiral polycyclic structures
The acid-catalyzed rearrangement of two enantiomerically pure epoxides derived from sesquiterpernic himachalenes, which are the main components of the essential oil of the Atlas cedar, has beenExpand
Catalytic enantioselective total synthesis of (−)-ar-Tenuifolene
Abstract First catalytic asymmetric total synthesis of aromatic sesquiterpene, (−)-ar-teunifolene (1) is featured (3 steps, 75% overall yields) from commercially available 3-methyl cyclohex-2-enoneExpand


Studies in sesquiterpenes—XXIX : Structure of himachalenes
α- and β-Himachalenes, the two major sesquiterpene components of the essential oil of Himalayan deodar (Cedrus deodara, Loud.) are shown to represent a new sequiterpenoid carbon framework. EvidenceExpand
Terpenoids—LX : Absolute configuration of ar-turmerone☆
Abstract The absolute configuration of (+) ar -turmerone is shown to be II on the basis of the optical rotatory dispersion curve of the (+)hydrocarbon (VII) derived from it. The molecular rotationsExpand
Terpenoids—LXIX: Absolute configuration of (−) α-curcumene☆
Abstract The absolute configuration of (+) 3- p -tolylbutanoic acid 2 (V) previously derived by the molecular rotation method has been confirmed by the conversion of (−) 3-phenylbutanoic acid 3 4Expand
Alicyclic-Aromatic Isomerization.