- An efficient stereocontrolled synthesis of methyl (9Z,11E,13S)-13-hydroxyoctadeca-9,11-dienoate (methyl coriolate)
-
An efficient synthesis of methyl (13S)-coriolate (S)-1b is accomplished by the palladium-catalyzed coupling of (1E,3S)-1-iodooct-1-en-3-ol [(S)-3] with methyl dec-9-ynoate (4) followed by selective reduction of the enyne (S)-2.
- Chemin,Linstrumelle
-
-
Read Online
- Asymmetric synthesis of 12-hydroxyheptadecatrienoic acid and its 5,6-dihydro- and 14,15-dehydro-derivatives
-
Natural 12-hydroxyheptadecatrienoic acid (12-HHT) with an S configuration was synthesised by a Suzuki-Miyaura coupling of C10-C17 iodo alcohol with C1-C9 vinylborane. The iodo alcohol was synthesised by utilising Sharpless asymmetric epoxidation of the corresponding trimethylsilyl alcohol. The method yielded more than 100 mg of 12-HHT. Similarly, syntheses of 5,6-dihydro- and 14,15-dehydro derivatives of 12-HHT, known as HHD and HHTE, respectively, were completed in a stereoselective manner.
- Kobayashi, Yuichi,Morita, Masao,Ogawa, Narihito,Kondo, Daiki,Tojo, Toshifumi
-
p. 10667 - 10673
(2016/11/30)
-
- Fully stereocontrolled syntheses of 3-oxacarbacyclin and carbacyclin by the conjugate addition-azoalkene-asymmetric olefination strategy
-
A fully stereocontrolled synthesis of 3-oxacarbacyclin (3) and a formal synthesis of carbacyclin (2) are described. The syntheses are based on the conjugate addition-azoalkene-asymmetric olefination strategy. Its key features are (1) the stereoselective e
- Kim, Mikhail,Gais, Hans-Joachim
-
p. 4642 - 4650
(2007/10/03)
-
- An efficient asymmetric synthesis of prostaglandin E1
-
An asymmetric total synthesis of Prostaglandin E1 (5) has been achieved in a two-component coupling process. The chiral hydroxycyclopentenone 6 was readily available from furan with 96% ee. The key reaction step was a kinetic enzymatic resolution followed by an in situ inversion. A catalytic asymmetric reduction of the γ-iodo vinyl ketone 19 with the Corey CBS catalyst gave the ω-side chain 7 with >96% ee. Conjugate addition using the reaction with dilithiocyanocuprate followed by mild cleavage of the silyl protective groups and enzymatic hydrolysis of the methyl ester 22 gave (-)-PGE1 5 in high yield.
- Rodriguez, Ana,Nomen, Miguel,Spur, Bernd Werner,Godfroid, Jean-Jacques
-
p. 2655 - 2662
(2007/10/03)
-
- Catalytic Asymmetric Addition of Polyfunctional Dialkylzincs to β-Stannylated and β-Silylated Unsaturated Aldehydes
-
The addition of functionalized dialkylzincs to readily available β-stannylated or β-silylated unsaturated aldehydes in the presence of a catalytic amount of (1R,2R)-1,2-bis(trifluorosulfonamido)cyclohexane (8 mol percent) provides chiral allylic alcohols
- Ostwald, Roswitha,Chavant, Pierre-Yves,Stadtmueller, Heinz,Knochel, Paul
-
p. 4143 - 4153
(2007/10/02)
-
- ENANTIOSELECTIVE SYNTHESIS OF 1-VINYL-1,2-DIOLS, VINYL EPOXIDES AND α,β-DIALKOXY ALDEHYDES
-
A practical synthetic method of chiral γ-trimethylsilylmethyl allylic alcohols (1) with both E- and Z-configuration has been developed.The alcohols 1 are readily converted into 1-vinyl-1,2-diols (5) via diastereoselective epoxidation followed by the react
- Matsumoto, Takashi,Kitano, Yasunori,Sato, Fumie
-
p. 5685 - 5688
(2007/10/02)
-
- A HIGHLY EFFICIENT SYNTHESIS OF OPTICALLY PURE γ-IODO ALLYLIC ALCOHOLS AND THEIR CONVERSION INTO VARIOUS OPTICALLY ACTIVE ALLYLIC ALCOHOLS
-
Kinetic resolution of γ-iodo allylic alcohols 1 by the Sharpless asymmetric epoxidation reaction proceeds with very large rate differences for the two enantiomers, thus providing a highly efficient method for preparation of optically pure 1.The alcohols 1
- Kitano, Yasunori,Matsumoto, Takashi,Wakasa, Takenori,Okamoto, Sentaro,Shimazaki, Toshiyuki,et al.
-
p. 6351 - 6354
(2007/10/02)
-
- A Highly Efficient Synthesis of Prostaglandin ω-Chain Precursors
-
Kinetic resolution of γ-tributylstannyl allylic alcohols by the Sharpless asymmetric epoxidation proceeds with synthetically satisfactory rate differences for the two enantiomers, thus providing a highly efficient method for the synthesis of prostaglandin
- Kitano, Yasunori,Matsumoto, Takashi,Okamoto, Sentaro,Shimazaki, Toshiyuki,Kobayashi, Yuichi,Sato, Fumie
-
p. 1523 - 1526
(2007/10/02)
-
- Synthetic Applications of the Enantioselective Reduction by Binaphthol-Modified Lithium Aluminum Hydride Reagents
-
The reduction of prochiral carbonyl substrates with the chiral binaphthol-modified lithium aluminum hydride reagents provides an effective means for preparing alcoholic products of high optical purity.The reaction is applicable to a variety of structurally diverse unsaturated carbonyl compounds such as aromatic ketones, acetylenic ketones, olefinic ketones and aldehydes, etc.Either of the antipodes is obtainable in a predictable manner by choosing the handedness of the auxiliary binaphthol ligand.The utility is exemplified by the efficiently stereocontrolled synthesis of prostaglandin intermediates, some insect pheromones, chiral primary terpenic alcohols, optically active styrene oxide, etc.
- Noyori, R.,Tomino, I.,Yamada, M.,Nishizawa, M.
-
p. 6717 - 6725
(2007/10/02)
-