108944-87-2Relevant academic research and scientific papers
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
Synthesis of decalin type chiral synthons based on enzymatic function
Nozawa,Murakami,Noda,Tamatsukuri,Kato,Akita
, p. 1176 - 1186 (2007/10/03)
Enzymatic monobenzoylation of (±)-2-hydroxy-decahydro-5,5,8a-trimethyl-1-naphthalenemethanol derivatives (1 - 4) using vinyl benzoate in organic solvent gave the optically active diols (1 - 4) and monobenzoates (16 - 19). The enantiomeric excess (ee) of t
Studies in lipase catalyzed transesterifications: Synthesis of (+)- albicanol, (+)-albicanyl acetate and chiral intermediates useful in the synthesis of drimanes and labdanes
Anilkumar,Sudhir, Uma,Joly,Nair, Mangalam S.
, p. 1899 - 1903 (2007/10/03)
Chiral intermediates [(-)-8, (+)-9, (-)-9, (+)-10, (-)-10, (+)-11] useful in the synthesis of drimanes and labdanes, as well as optically active albicanol 1 and albicanyl acetate 2, have been synthesized using enzymatic transesterification as the key step. (C) 2000 Elsevier Science Ltd.
Total synthesis of both enantiomers of copalol via optical resolution of a general synthetic intermediate for drimane sesquiterpenes and labdane diterpenes
Toshima, Hiroaki,Oikawa, Hideaki,Toyomasu, Tomonobu,Sassa, Takeshi
, p. 8443 - 8450 (2007/10/03)
The total synthesis of both enantiomers of copalol (6) was accomplished via the optical resolution of a racemic diol [(±)-4] which is a general synthetic intermediate for drimane sesquiterpenes and labdane diterpenes. Esterification between (±)-4 and Boc-L-proline gave the diastereomeric pair of monoesters (5a and 5b) which could be readily separated by flash column chromatography. PDC-oxidation of the resolved 5a and 5b, and subsequent β-elimination gave optically active enones (9 and ent-9). Both enones were respectively converted into (+)-6 in 36% yield and (-)-6 in 26% yield in five steps: (1) Sakurai reaction (TiC14-promoted conjugate addition of allylsilane), (2) Wittig methylenation, (3) Wacker oxidation, (4) Horner-Emmons reaction, and (5) DIBAL-H reduction. (C) 2000 Elsevier Science Ltd.
Simple approach to optically active drimane sesquiterpenes based on enzymatic resolution
Akita, Hiroyuki,Nozawa, Masako,Futagami, Yoshiko,Miyamoto, Maiko,Saotome, Chikako
, p. 824 - 831 (2007/10/03)
When the β-acyloxy esters (±)-10 and (±)-II were exposed to the lipase OF-360 from Candida rugosa or immobilized lipase OF-360 in a water- saturated organic solvent, the hydrolyzed product (8aS)-6 was obtained in high chemical (40%) and optical (>99%ee) yields. The absolute structure of (8aS)-6 was confirmed by the fact that (8aS)-6 was converted into an authentic sample γ-keto nitrile (8aS)-17. Treatment of the diol (±)-12 with isopropenyl acetate in the presence of the lipase Godo E-4 from Pseudomonas sp. provided the unchanged (8aR)-12 (89% ee) in 42% yield.
STUDIES TOWARD THE TOTAL SYNTHESIS OF POLYOXYGENATED LABDANES: PRELIMINARY APPROACHES
Herlem, Denyse,Kervagoret, Jocelyne,Dahai, Yu,Khuong-Huu, Francoise,Kende, Andrew S.
, p. 607 - 618 (2007/10/02)
Using the keto-ester 3 as a starting material, methods are developed for the successive introduction of hydroxy groups at C-6, C-7 and C-8 of a decalin system, as well as for elaboration of a C-9 pentadiene chain in preliminary approach to the total synthesis of trihydroxylabdadienes.
A formal synthesis of (±)-Ambrox
Snowden,Linder
, p. 4119 - 4120 (2007/10/02)
Bicyclic diol 6, a direct precursor of (±)-Ambrox ((±)-7), has been synthesised in four steps (35% yield) from the known bicyclic enone 2.
