16892-20-9Relevant articles and documents
Synthesis of Cyclohexanones through a Catalytic Cationic Cyclization of Alkynols or Enynes
Alonso, Pedro,Fontaneda, Raquel,Pardo, Pilar,Fa?anás, Francisco J.,Rodríguez, Félix
supporting information, p. 1659 - 1662 (2018/03/23)
A novel procedure for the synthesis of cyclohexanones from alkynol or enyne derivatives through a cationic cyclization has been developed. The key points to obtain the six-membered ring derivatives are the use of starting materials containing a terminal alkyne, the use of tetrafluoroboric acid as a promoter of the cationic cyclization, and the appropriate selection of 1,1,1,3,3,3-hexafluoropropan-2-ol (HFIP) as solvent. This strategy can be extended to the biomimetic cationic cyclization of several terpene-derived polyenynes.
NOVEL 1H- SPIRO [NAPHTALENE- 2, 2 ' -OXIRANE] DERIVATIVES
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Page/Page column 7, (2012/06/15)
Compounds of formula (I), wherein R1 is hydrogen, methyl or ethyl, and R2 is methyl or ethyl, having woody and ambery odor notes, their use as fragrance ingredient and perfumed products comprising them.
An efficient approach to chiral nonracemic trans- and cis-decalin scaffolds for drimane and labdane synthesis
Pollini, Gian Piero,Bianchi, Anna,Casolari, Alberto,De Risi, Carmela,Zanirato, Vinicio,Bertolasi, Valerio
, p. 3223 - 3231 (2007/10/03)
Optically active trans- and cis-ring junction decalinic intermediates, which represent useful precursors for the synthesis of more complex natural targets, have been conveniently prepared starting from the β-ketoester 2 obtained by standard chemistry from
Partial Synthesis of ( - )-11,12-Dinordriman-8-one and the ( - )-Enantiomer of Polywood
Cortes, Manuel,Moreno, Luis,Lopez, Jose
, p. 36 - 37 (2007/10/03)
A chiral sequiterpene diol 6, readily available from the natural product polygodial (4), has been used for the first partial synthesis of the title compounds.
Enantioselective syntheses of (2S,4AS,8aR)-1,1-4a-trimethyldecahydronaphthalen-2-ol[(-)-TMD], (4aS,8aR)-5,58a-trimethyloctahydronaphthalen-2(1H)-one, and (-)-Polywood, through Michael-type reaction of chiral imines
Jabin, Ivan,Revial, Gilbert,Melloul, Karine,Pfau, Michel
, p. 1101 - 1109 (2007/10/03)
The title compounds 6, 15, and 17 have been synthesized in a straightforward way in good yields and high enantiomeric excesses by the chiral imines method, leading to building-blocks 2 and 10, followed by a few conventional steps.
Acid-Mediated Cyclisations: Efficient Access to Functionalised trans-Decalins
Linder, Simon M.,Reichlin, Daniel,Simmons, Dana P.,Snowden, Roger L.
, p. 4789 - 4792 (2007/10/02)
Acid-mediated cyclisation of monocyclic, (E)- and (Z)-β-phosphoroxyenoate 5d using 98percent aq.H2SO4 in toluene at 2 deg C affords, after decarbomethoxylation, trans-2-decalone 1 in 79percent and 68percent yield, respectively.Key Words: cyclisation; deca
The synthesis of chiral decalones, (-)-1,1,4a-trimethyl-2-decalol and (+)-geosmin from S-(+)-carvone (part 3)
Swarts, Henk J.,Haaksman, Anja A.,Jansen, Ben J. M.,De Groot, Aede
, p. 5497 - 5508 (2007/10/02)
The cholesterol biosynthesis inhibitor (-),1,1,4a-trimethyl-2-decalol (4), the chiral decalones 6 and 7, and (+)-geosmin (9 were synthesized from S-(+)-carvone. Annelation of S-(-)-dihydrocarvone followed by methylation gave compound 8 which was used as a
Acid-Catalysed Double Bond Isomerisation of 8a-Substituted 5,5-Dimethyl-3,5,6,7,8,8a-hexahydro-2(1H)-naphthalenones
Kato, Michiharu,Vogler, Bernhard,Yoshikoshi, Akira
, p. 953 - 979 (2007/10/02)
On equilibrium with acid, deconjugated octalones, (17) and (18), possessing an alkyl substituent at the angular position gave good yields of a mixture of cis- and trans-conjugated octalones, (25 and 26) and (27 and 28), respectively, in almost equal ratios, whereas deconjugated octalones having an oxygenated angular substituent provided good yields of cis-conjugated octalones, i.e., (23) stereoselectively from (15), and (21) exclusively from (13).Stereochemical assignment of the conjugated octalones obtained was readily established by comparison of characteristic allylic coupling constants (J3,4a) in their 1H NMR spectra.The conformation of the cis-conjugated octalones was deduced to be steroidal on the basis of the very small magnitude of J3,4a ( 1 Hz).
DIASTEREOCONTROLLED SYNTHESIS OF FUNCTIONALIZED TRANS-DECALINS VIA ELECTROCYCLIC REACTION OF TRIENOL ETHERS
Fehr, Charles,Galindo, Jose,Guntern, Olivier
, p. 4021 - 4024 (2007/10/02)
(E)-Trienol silyl ethers 10 and 11, selectively prepared by mono-Grignard reaction on methyl β-cyclogeranate (7) or by deprotonation of enone 8 were transformed to trans-decalins 5 and 6 by a thermal electrocyclic reaction.The hithero unknown enones 5 and 6 exhibit interesting organoleptic properties and show promise as versatile synthetic intermediates.The herein described transformation opens a new route for the direct construction of C(6)-functionalized drimanes such as cinnamodial (3) and forskolin (4).
Configuration-Odor Relationship in 5β-Ambrox
Escher, Sina,Giersch, Wolfgang,Niclass, Yvan,Bernardinelli, Gerald,Ohloff, Guenther
, p. 1935 - 1947 (2007/10/02)
The four possible A/B cis-fused diastereomers of Ambrox have been synthesized and their configurations and conformations established by X-ray and NMR analysis.Only 5β-ambrox (=1,2,3a,4,5,5aβ,6,7,8,9,9a,9bα-dodecahydro-3aβ,6,6,9aβ-tetramethylnaphthofuran; 5) has an odor quality comparable to Ambrox.The 1,3-synperiplanar/diaxial conformation of the substituents at C(8) (=C(3a)) and C(10) (=C(9a)) has thus been confirmed to be a compulsory structure element for the particular odor.
