171335-60-7Relevant academic research and scientific papers
Stereoselective total synthesis of cananginones (D-I) using Ireland-Claisen rearrangement as a key step
Kuilya, Tapan Kumar,Chatterjee, Shamba,Goswami, Rajib Kumar
, p. 2905 - 2918 (2014/04/17)
A strategy for stereoselective total synthesis of α-substituted γ-hydroxymethyl γ-butyrolactone containing bioactive natural products cananginones (D-I) has been developed using cheap and commercially available d-mannitol as a chiral pool. The Ireland-Cla
Stereoselective total synthesis of xyolide
Reddy, B.V. Subba,Reddy, P. Sivaramakrishna,Reddy, B. Phaneendra,Yadav,Al Khazim Al Ghamdi, Ahamad
, p. 5758 - 5760 (2013/09/24)
A stereoselective total synthesis of xyolide is described employing MacMillan α-hydroxylation, Steglich esterification, and ring closing metathesis as key steps. The use of organocatalytic MacMillan α-hydroxylation to construct two of the chiral centers o
PEGYLATED LIPIDS AND THEIR USE FOR DRUG DELIVERY
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Page/Page column 127-128, (2012/08/07)
The invention provides poly(ethylene glycol)-lipid conjugates for use in drug delivery.
Halocarbocyclization entry into the oxabicyclo[4.3.1]decyl exomethylene-δ-lactone cores of linearifolin and zaluzanin A: Exploiting combinatorial catalysis
Ginotra, Sandeep K.,Friest, Jacob A.,Berkowitz, David B.
, p. 968 - 971 (2012/04/04)
A streamlined entry into the sesquiterpene lactone (SQL) cores of linearifolin and zaluzanin A is described. Stereochemistry is controlled through transformations uncovered by ISES (In Situ Enzymatic Screening). Absolute stereochemistry derives from kinet
The stereoselective total synthesis of (+)-stagonolide B
Srihari, Pabbaraja,Kumaraswamy, Boyapelly,Somaiah, Ragam,Yadav, Jhillu S.
experimental part, p. 1039 - 1045 (2010/04/29)
The stereoselective total synthesis of the nonenolide, (+)-stagonolide B is described. The key steps involve epoxide homologation, hydrolytic kinetic resolution and ring-closing metathesis.
Ring-conformer effects of the cyclopropyl group: First use of trans-(2r,3r)-cyclopropanecarbaldehydes as electrophiles in diastereoselective baylisihillman reaction
Krishna, Palakodety Radha,Kishore,Reddy, P. Srinivas
scheme or table, p. 2605 - 2608 (2010/03/03)
trans-(2R,3R)-Cyclopropanecarbaldehydes are used as novel electrophiles in the Baylis-Hillman reaction to afford adducts in good yields (75-85%) and diastereoselectivities (60-90%).
Synthesis of the core structure of apicularen a by transannular cyclization.
Kuehnert, Sven M,Maier, Martin E
, p. 643 - 646 (2007/10/03)
[reaction: see text] An approach to the macrocyclic core of apicularen A is described. Thus, cross-coupling of the aryl triflate 7 with the vinylstannane 19 provided the styrene 20. Deprotection led to the dihydroxy acid 22. Through a size-selective macro
Preparation of optically active diol derivatives by the enzymatic hydrolysis of cyclic carbonates
Matsumoto, Kazutsugu,Fuwa, Seiji,Shimojo, Megumi,Kitajima, Hidehiko
, p. 2977 - 2987 (2007/10/03)
A simple enzymatic method for the preparation of optically active 1,2- and 1,3-diol derivatives is disclosed. In the screening of enzymes, racemic 4-[(2-benzyloxy)ethyl]-1,3-dioxolan-2-one (1a) was enantioselectively hydrolyzed by porcine pancreas lipase (PPL) to give optically active (R)-1a and (S)-4-(benzyloxy)butane-1,2-diol (2a). The addition of 10% i-PT2O to the reaction system dramatically improved the reactivity to afford optically pure (A)-1a in 31% yield. PPL also catalyzed the hydrolysis of several five-membered cyclic carbonates with high enatioselectivity. It is noteworthy that the increment of the carbon number of the substituents reflects the drastic increase in enantioselectivity. On the other hand, the hydrolyses of six- and seven-membered cyclic carbonates were also catalyzed by PPL. In particular, the reaction of a six-membered substrate enantioselectively proceeded. This reaction afforded optically active 1,3-diol derivatives which could not be directly prepared by hitherto known methods using hydrolytic enzymes.
Enzyme-mediated enantioselective hydrolysis of cyclic carbonates
Matsumoto, Kazutsugu,Fuwa, Seiji,Kitajima, Hidehiko
, p. 6499 - 6502 (2007/10/02)
The enzyme-mediated enantioselective hydrolysis of cyclic carbonates is disclosed. Racemic 4-(2-benzyloxy)ethyl-1,3-dioxolan-2-one (1a) was enantioselectively hydrolyzed by porcine pancreas lipase (PPL) to give optically active (R)-1a and (S)-4-benzyloxybutane-1,2-diol (2a). PPL also catalyzed the hydrolysis of several five-membered cyclic carbonates with high enantioselectivity.
Functionalized Diorganozinc Compounds: Key Reagents for the Synthesis of Enantiomerically Pure 2,5-Disubstituted cis- and trans-Tetrahydrofurans
Berninger, Joern,Koert, Ulrich,Eisenberg-Hoehl, Christina,Knochel, Paul
, p. 1021 - 1028 (2007/10/03)
1,4-Diol derivatives 4a-i were synthesized stereoselectively by either reagent- or catalyst-controlled routes using the addition of functionalized diorganozinc reagents to aldehydes.The stereoselectivities along the reagent-controlled synthetic path were in the range between 80:20 and 95:5.The stereoselectivities along the catalyst route exceeded 95:5.The 1,4-diol derivatives 4 thus obtained were transformed into enantiomerically pure cis- and trans-2,5-disubstituted tetrahydrofurans (16-20) by means of an intramolecular Williamson reaction. - Keywords: Synthesis, stereoselective / Catalysis / Tetrahydrofurans / Dialkylzinc reagents
