- Methods and systems for evaluating and predicting the reactivity of monooxygenase enzymes
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Methods and systems for evaluating and predicting the reactivity of natural and engineered monooxygenase enzymes are provided. Methods are provided for acquiring a functional profile (fingerprint) of monooxygenases that encode information regarding the ac
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Page/Page column 45
(2016/04/20)
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- Process for the preparation of substituted pyrrolidine derivatives and intermediates
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Two syntheses are provided; one for the preparation of (3R,4R)-4-(hydroxymethyl)pyrrolidin-3-ol, and other for the preparation of (3S,4R)-4-(hydroxymethyl)pyrrolidin-3-ol. (3R,4R)-4-(hydroxymethyl)pyrrolidin-3-ol is prepared using the achiral ylide prepared from benzylamine instead of phenethylamine (Scheme 3) which provides a crystalline intermediate. The synthesis of (3S,4R)-4-(hydroxymethyl)pyrrolidin-3-ol is achieved from (S)-diethylmalate as described in Scheme 4. A process for preparing camphor sultam is also provided.
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Page/Page column 7
(2010/11/08)
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- A practical large-scale synthesis of (3R,4R)-4-(Hydroxymethyl)pyrrolidin-3- ol via asymmetric 1,3-dipolar cycloaddition
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(3R,4R)-4-(Hydroxymethyl)pyrrolidin-3-ol (1), which is a useful intermediate for the synthesis of various bioactive molecules, has been synthesized in 51% overall yield by 1,3-dipolar cycloaddition reaction from the dipolarophile, (E)-3-benzyloxypropenoyl-(2′S)-bornane-10,2-sultam (5), and the achiral ylide precursor, N-(benzyl)-N-(methoxymethyl)-N- (trimethylsilylmethyl)amine (6), without using chromatography and the subsequent reduction with LAH and catalytic hydrogenation. The diastereomers 7 and 8 were separated by crystallization, and efficient procedures were developed for the subsequent reactions to afford 1.
- Kotian, Pravin L.,Lin, Tsu-Hsing,El-Kattan, Yahya,Chand, Pooran
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p. 193 - 197
(2012/12/24)
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- Progress toward the total synthesis of callipeltin A (I): Asymmetric synthesis of (3S,4R)-3,4-dimethylglutamine
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(equation presented) During the total synthesis of the novel cyclic depsipeptide callipeltin A (1), the unit (3S,4R)-3,4-dimethylglutamine, was successfully synthesized by asymmetric Michael addition and subsequent electrophilic azidation. The key feature of this approach is the generation of three adjacent stereogenic centers using the same camphorsultam chiral auxiliary.
- Liang, Bo,Carroll, Patrick J.,Joullie, Madeleine M.
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p. 4157 - 4160
(2007/10/03)
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- Novel application of chiral micellar media to the Diels-Alder reaction
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A novel chiral surfactant has been used in the first reported aqueous chiral micellar catalysis of a Diels-Alder reaction and enantioselectivities have been observed.
- Diego-Castro, Michael J.,Hailes, Helen C.
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p. 1549 - 1550
(2007/10/03)
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- IRIDOIDS : ENANTIOSELECTIVE SYNTHESIS OF LOGANIN VIA AN ASYMMETRIC DIELS-ALDER REACTION
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Starting from (-)-camphor-10-sulfonic acid (5) the crystalline sultam 9 was readily prepared.TiCl4-mediated Diels-Alder addition of the N-crotonyl sultam 11 to cyclopentadiene, crystallization of the resulrting adduct 12 and subsequent reduction gave virtually pure (1S, 4R,5R, 6S)-1 together with recovered auxiliary 9.The loganin precursor 1 was transformed into norbonanone 20, which upon Baeyer-Villiger oxidation led to the suitably substituted cyclopentane 22 from which 1-B-O-methyl loganin aglucone (2) was readily available.
- Vandewalle, M.,Van der Eycken, J.,Oppolzer, W.,Vullioud, C.
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p. 4035 - 4044
(2007/10/02)
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- Camphor-Derived N-Acryloyl and N-Crotonoyl Sultams: Practical Activated Dienophiles in Asymmetric Diels-Alder Reactions
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Starting from (+)-camphor-10-sulfonyl chloride (5), the crystalline sultam 8 was easily prepared.Lewis-acid-promoted Diels-Alder additions of the crystalline N-acryloyl and N-crotonoyl derivatives 9 and 10, respectively, to cyclopentadiene and 1,3-butadiene at -130 to -78 grad furnished adducts 11, 12 and 17 with high chiral efficiency.Crystallization of the adducts and nondestructive removal of 8 gave either alcohols 13, 14 and 18 or acid 19 in 99percent enantiomeric purity.The sense of induction was reversed on using the enantiomer of 8 as the auxiliary.The structure of 10 was established by X-ray diffraction analysis
- Oppolzer, Wolfgang,Chapuis, Christian,Bernardinelli, Gerald
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p. 1397 - 1401
(2007/10/02)
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