4895-33-4Relevant academic research and scientific papers
Synthesis based on cyclohexadienes. Part 21. Total synthesis of (±)-hinesol and (±)-10-epi-hinesol
Janaki, Seenivasaga N.,Subba Rao
, p. 195 - 200 (1997)
An efficient strategy for the construction of the spiro[4.5]decane and eremane systems is described which involves an acid-catalysed rearrangement of an endo alcohol, followed by an oxidative cleavage resulting in the generation of a spiro-system, as the key step. This methodology is extended to the total synthesis of (±)-hinesol and (±)-10-epi-hinesol 2.
A unified, RCM anchored approach to spiro[4.5]decane-based sesquiterpenoids: Collective synthesis of (±)-α & β-vetispirenes, (±)-β-vetivone, (±)-agarospirol and (±)-hinesol
Athe, Sudhakar,Ghosh, Subhash,Mehta, Goverdhan
, p. 1570 - 1573 (2019/05/22)
Collective syntheses of five spiro[4.5]decane framework bearing sesquiterpenoids, namely, α & β-vetispirenes, β-vetivone, agarospirol and hinesol as well as formal synthesis of axenol and gleenol from a readily available precursor cyclohexanone-β-ketoester via the intermediacy of a versatile intermediate (2,10-dimethylspiro[4.5]dec-1-en-6-one) have been accomplished in a concise manner.
Claisen rearrangement strategy in alkenyl dihydropyran leading to total synthesis of (+)-α-vetispirene and (-)-agarospirol
Nakazaki, Atsuo,Kobayashi, Susumu
, p. 42 - 43 (2007/10/03)
Total synthesis of (+)-α-vetispirene and (-)-agarospirol based on a Claisen rearrangement has been achieved. This is the first example of a Claisen rearrangement in an enantio-enriched alkenyl bicyclic dihydropyran system with perfect asymmetric transmission. Copyright
Stereoselective total synthesis of (±)-α-vetispirene, (±)-hinesol, and (±)-β-vetivone based on a Claisen rearrangement
Nakazaki, Atsuo,Era, Tomohiro,Numada, Yuko,Kobayashi, Susumu
, p. 6264 - 6271 (2007/10/03)
The stereoselective total syntheses of (±)-α-vetispirene, (±)-hinesol, and (±)-β-vetivone were accomplished based on a Claisen rearrangement in an alkenyl bicyclic dihydropyran system. The most striking feature of this approach is that the Claisen rearrangement of bicyclic dihydropyran proceeds stereoselectively to provide a multi-functionalized spiro[4.5]decane, which is an efficient precursor for the synthesis of the vetivane sesquiterpenes.
Connective synthesis of spirovetivanes: Total synthesis of (±)-agarospirol, (±)-hinesol and (±)-α-vetispirene
Maulide, Nuno,Vanherck, Jean-Christophe,Marko, Istvan E.
, p. 3962 - 3967 (2007/10/03)
A concise, connective synthesis of naturally occurring spirovetivanes 1 and 3, in racemic form, is presented. This novel approach involves the efficient assembly of the advanced intermediate 12 through a unique spiroannulation protocol. Wiley-VCH Verlag GmbH & Co. KGaA1 69451 Weinheim, Germany, 2004.
A phosphine-catalyzed [3+2] cycloaddition strategy leading to the first total synthesis of (-)-hinesol
Du, Yishu,Lu, Xiyan
, p. 6463 - 6465 (2007/10/03)
In one step, the skeleton of cis-spirovetivanes was constructed with high stereoselectivity by the phosphine-catalyzed [3+2] cycloaddition reaction of tert-butyl 2,3-butadienoate or 2-butynoate with 3-methyl-2-methylenecyclohexanone (5). This method was exemplified by the first highly efficient total synthesis of natural product (-)-hinesol, which is an active ingredient of cerebral circulation and metabolism improvers.
Synthetic photochemistry. LXVII. A total synthesis of (±)-hinesol and (±)-agarospirol via retro-benzilic acid rearrangement
Hatsui,Wang,Takeshita
, p. 2393 - 2399 (2007/10/02)
A mild base-catalyzed retro-benzilic acid rearrangement of a proto-photocycloadduct, formed in highly stereoselective photoaddition of methyl 2,4-dioxopentanoate to 1,5-dimethyl-6-methylene-1-cyclohexene, afforded a spiro[4.5]decenedione derivative. Reductive elimination of the α-dicarbonyl function and C1-homologation furnished (±)-hinesol and (±)-agarospirol.
A NOVEL SKELETAL REARRANGEMENT OF BICYCLO(2.2.2)OCTENES THROUGH BICYCLO(3.2.1)OCTENE SYSTEM: SYNTHESIS OF (+/-)-HINESOL AND (+/-)-10-epi-HINESOL
Rao, G.S.R. Subba,Janaki, Seenivasaga N.
, p. 3105 - 3108 (2007/10/02)
Acid catalysed rearrangement of the endo-alcohol (9) leads to the ketones (11) and (12) having the bicyclo(3.2.1) and bicyclo(2.2.2) moieties.An efficient entry into spiro(4,5)decane and eremane system, as exemplified by the total synthesis of (+/-)-hinesol (2) and its 10-epimer (3) is reported.
A New Synthesis of (+/-)-Agarospirol and (+/-)-Hinesol
Iwata, Chuzo,Ida, Yasuo,Miyashita, Kazuyuki,Nakanishi, Tsutomu,Yamada, Minoru
, p. 2738 - 2741 (2007/10/02)
(+/-)-Agarospirol (8) and (+/-)-hinesol (9) were simultaneously synthesized via a useful synthon in the synthesis of spirovetivane-type sesquiterpenes, i.e., (2S*,5S*,10R*)-2-hydroxy-6,10-dimethylspirodec-6-en-8-one (1), which had previously been prepared from the corresponding phenolic α-diazoketone via the spiro-annelation reaction and subsequent stereo-controlled Birch reduction, both reported in our previous communications.Keywords-(+/-)-agarospirol; (+/-)-hinesol; spirovetivane-type sesquiterpenes; useful synthon; (2S*,5S*,10R*)-2-hydroxy-6,10-dimethylspirodec-6-en-8-one
The total synthesis of (+/-)hinesol and (+/-)epihinesol
Lafontaine, Jacques,Mongrain, Marcel,Sergent-Guay, Mireille,Ruest, Luc,Deslongchamps, Pierre
, p. 2460 - 2476 (2007/10/02)
The tricyclic ketal ketones 15a and 15b have been obtained in an isomeric ratio of 9:1 (4 5 6 7 8 9 10 11 12 13 14 15a + 15b).Compound 15a was converted in seven (or eight) steps to (+/-)epihinesol (3) 29 32 48 49 47 (or 32 39 38 44 47) 50 3> and compound 38 was transformed into (+/-)hinesol (2) in five steps (38 76 77 62 63 2).The identity of epihinesol and agarospirol was confirmed by formation of a common epoxide.
