53834-70-1Relevant academic research and scientific papers
Synthesis of (+/-)-Hotrienol and (+/-)-Santolina Alcohol via Cyclopropenes
Moiseenkov, Alexander M.,Czeskis, Boris A.,Semenovsky, Alexei V.
, p. 109 - 110 (1982)
A short synthesis of the title monoterpenols via cyclopropylcarbinyl-homoallyl rearrangement of adducts which are themselves produced by tandem addition of vinylmagnesium bromide and an appropriate carbonyl compound to the cyclopropenes (1) is described.
A practical and convenient synthesis of hotrienol, an excellent fruity smelling compound
Yuasa, Yoshifumi,Kato, Yasushi
, p. 4036 - 4039 (2007/10/03)
The practical and convenient synthesis of hotrienol, which is an excellent fruity smelling compound, has been performed by the ene-type chlorination of linalyl acetate and then dehydrochlorinated by lithium bromide and lithium carbonate in DMF, followed by hydrolysis in three steps with an overall yield of 55%.
Regioselective synthesis of substituted (3E)-1,3-dienes from chelated allyl-ironcarbene complexes and potassium enoxyborates
B?hmer, Jutta,Hampel, Frank,Schobert, Rainer
, p. 661 - 667 (2007/10/03)
The addition of potassium enoxyborates to the chelated allyl-ironcarbene complex 1 leads to the corresponding η-(3E)-1,3-diene complexes 2 in fair yields. Complexes 2 can be demetalated with ceric ammonium nitrate (CAN) to give unrearranged (3E)-6-oxo-1.3-dienes 3. Prior to decomplexation, the carbonyl group can be further modified. This is demonstrated by the syntheses of the natural terpene alcohol hotrienol and of a complexed methylene- separated dienyne. Potassium enoxyborates are superior to lithium enolates as they are readily prepared in situ from a variety of aldehydes and ketones which do not form sufficiently stable lithium derivatives. In contrast to lithium enolates, only C- C coupling products derived from the 'kinetic' regioisomers are formed from unsymmetrical aliphatic ketones.
REGIOSELECTIVITY AND SYNTHETIC APPLICATION OF THE HYDROALUMINATION OF 2-METHYL-1-ALKEN-3-YN-6-OLS. UNEXPECTED INVERSION OF CONFIGURATION IN THE SUBSTITUTIVE METHYLATION OF (Z)-3-IODO-2-METHYL-1,3-ALKADIEN-6-OLS
Khrimyan, A. P.,Garibyan, O. A.,Makaryan, G. M.,Panosyan, G. A.,Badanyan, Sh. O.
, p. 895 - 901 (2007/10/02)
With the use of the deuterated reagents LiAlD3(OCH)3 and D2O, and also of electrophilic iodination, the regioselectivity of the hydroalumination of β-enynols with lithium trihydridomethoxyaluminate was studied.Attack by the hydride ion goes to the extent of 90percent at the Cβ atom of the enynols.The synthesis of the natural monoterpenol (+/-)-hotrienol and allied compounds was carried out.By a combination of hydroalumination-iodination and substitutive methylation a new method was developed for the building of the (Z)-2,3-dimethyl-1,3-diene fragment.The unexpected complete (90-95percent) inversion of the Z-double bond in the methylation of iodo dienols with lithiium dimethylcuprate was established.
Structure and the Synthesis of Novel Constituents of Yudzu Peel Oil and Their Conversion to Related Monoterpenes
Kitahara, Takeshi,Takagi, Yoshikazu,Matsui, Masanao
, p. 897 - 902 (2007/10/02)
Two novel minor components isolated from yudzu peel oil were characterized as monoterpene β-ketols, 1 and 3, by their synthesis, and they were converted to related monoterpenes, dihydroneroloxide (9) neroloxide (10) and ho-trienol (11).
