38965-62-7Relevant academic research and scientific papers
Total Synthesis of (+)-Blastmycinone, (-)-Litsenolide C1, and Related Natural Trisubstituted Lactones via Alkynyltungsten Compounds
Chen, Ming-Jung,Lo, Ching-Yu,Chin, Chih-Chien,Liu, Rai-Shung
, p. 6362 - 6367 (2000)
A general method for total synthesis of natural trisubstituted γ-lactones is developed on the basis of the chemistry of alkynyltungsten compounds. The key step in this approach involves the cycloalkenation of tungsten-η1-(3R,4S)-pent-1-yne-3,4-diol with aldehydes to give tungsten-oxacarbenium salts, further leading to 3-alkylidene-4-hydroxy-5-methyl-y-lactones upon demetalation. This synthetic sequence proceeds well for alkynylaldehydes and the MOM derivative of tungsten-η1-(3R,4S)-pent-1-yne-3,4-diol. The resulting butyrolactone products are transformed into natural trisubstituted butyrolactones including (+)-blastmycinone, (+)-blastmycinolactol, (+)-antimycinone, NFX-2, and (+)-isodihydromahubanolide A. By using the same approach based on (R)-ethyl lactate, the natural (-)-litsenolide C1 can be prepared in a few steps.
The Total Synthesis of (-)-Litsenolides C-1 and C-2
Wood, William W.,Watson, Graham M.
, p. 2681 - 2688 (2007/10/02)
The total synthesis of (-)-litsenolides C1 and C2 from D-glucose in 12percent overall yield is described in which the α-alkylidene double-bond is formed by a Wittig reaction of a C-2 oxocarbohydrate derivative.
Synthesis of Optically Active Litsenolide C
Wakabayashi, Shoji,Ogawa, Hideki,Ueno, Naomi,Kunieda, Norio,Mandai, Tadakatsu,Nokami, Junzo
, p. 875 - 878 (2007/10/02)
Lithium enolate, derived from alkyl 2-(phenylthio)alkanoate with lithium diisopropylamide, reacted with aldehyde in the presence of diethylaluminum chloride to give alkyl 2-phenylthio-2-alkyl-3-hydroxyalkanoate, which was converted to 2-alkylidene-3-hydro
The Total Synthesis of Litsenolides C1 and C2
Wood, William W.,Watson, Graham M.
, p. 1599 - 1600 (2007/10/02)
Naturally occurring α-alkylidene-γ-butyrolactones can be prepared from a carbohydrate precursor using Wittig methodology to form the exocyclic double bond.
A SHORT STEREOSELECTIVE SYNTHESIS OF (+/-)-LITSENOLIDES C1 AND C2.
Barbier, Pierre,Benezra, Claude
, p. 3513 - 3516 (2007/10/02)
A five-step synthesis of the above substances from ethyl phenylthioacetate and 1-bromotetradecane is described.
The Total Synthesis of Lauraceae Lactones: Obtusilactones, Litsenolides, and Mahubanolides
Rollinson, Susan Wells,Amos, Richard A.,Katzenellenbogen, John A.
, p. 4114 - 4125 (2007/10/02)
The total synthesis of obtusilactones (1a,b, 2a,b), mahubanolides (1c, 2c), epilitsenolides (5b, 6b), and dihydromahubanolides (4c, 5c, 6c) is described.The enolates derived from the α-phenylselenenyl esters (17a-c) were used as acrylate α-anion synthons; aldol addition to propargylaldehyde, followed by oxidation to the selenoxide and elimination, furnished the isomeric acetylenic esters 20a-c and 21a-c.In a similar manner, aldol addition to acrolein followed by oxidation/elimination yielded olefinic esters 18b,c and 19b,c.The acetylenic esters were saponified, and the corresponding carboxylic acids were converted by either mercuric ion-catalyzed or bicarbonate-catalyzed lactonization to the obtusilactones (1a,b, 2a,b) and mahubanolides (1c, 2c).The olefinic esters were saponified, and the corresponding carboxylic acids lactonized to γ-substituted lactones (30b,c, 32b,c 32c) by treatment with either phenylselenenyl chloride or iodine.The epilitsenolides (5b, 6b) and dihydromahubanolides (5c, 6c) were then obtained by treating the substituted γ-lactones with tri-n-butyltin hydride.Homogeneous catalytic hydrogenation (Rh(PPh3)3Cl) of isomahubanolide (2c) gave a mixture of dihydromahubanolides 4c and 6c.
SYNTHESIS OF (+/-)-LITSENOLIDE C1
Vollenberg, Robert H.
, p. 3139 - 3142 (2007/10/02)
The β-hydroxy-γ-methyl-α,β'-unsaturated-γ-lactone, litsenolide C1, was synthesized in a highly stereoselective approach.
