155418-40-9Relevant articles and documents
Synthesis of the spiroacetal core of the cephalosporolide family of natural products
Finch, Orla C.,Furkert, Daniel P.,Brimble, Margaret A.
supporting information, p. 590 - 596 (2014/02/14)
The synthesis of four possible stereoisomers of the spiroacetal core of the natural products cephalosporolides H and I and penisporolides A and B is described. The key steps involve the use of Sharpless asymmetric dihydroxylation to install the desired stereochemistry of the γ-lactone ring and an oxidative radical cyclisation to form the spiroacetal ring system.
Development of a robust procedure for the copper-catalyzed ring-opening of epoxides with Grignard reagents
Alam, Mahbub,Wise, Christopher,Baxter, Carl A.,Cleator, Ed,Walkinshaw, Andrew
experimental part, p. 435 - 441 (2012/07/31)
A general procedure for the copper-catalyzed regioselective ring-opening of epoxides with Grignard reagents is described. The procedure developed provides robust reaction conditions which limit the formation of impurities and has been applied successfully using a series of epoxides and Grignard reagents to provide the desired products in >90% yield with excellent regioselectivity and purity.
Stereoselective synthesis of the C1-C16 fragment of goniodomin A
Nakajima, Motohiro,Fuwa, Haruhiko,Sasaki, Makoto
, p. 948 - 956 (2012/11/07)
Stereoselective synthesis of the C1-C16 fragment of the antifungal marine polyether macrolide goniodomin A is described. A Stille-type coupling of organostannanes and thioesters was exploited as the key carbon-carbon bondforming process, namely for the fo
A convergent synthesis of the C1-C16 segment of goniodomin A via palladium-catalyzed organostannane-thioester coupling
Fuwa, Haruhiko,Nakajima, Motohiro,Shi, Jinglu,Takeda, Yoshiyuki,Saito, Tomoyuki,Sasaki, Makoto
supporting information; experimental part, p. 1106 - 1109 (2011/04/24)
A convergent synthesis of the C1-C16 segment of goniodomin A, an actin-targeting marine polyether macrolide natural product, has been achieved via a 2-fold application of palladium-catalyzed organostannane-thioester coupling.(Figure Presented)
Algal pheromone biosynthesis: Stereochemical analysis and mechanistic implications in gametes of ectocarpus siliculosus
Rui, Fabio,Boland, Wilhelm
supporting information; experimental part, p. 3958 - 3964 (2010/08/22)
During sexual reproduction, female gametes or eggs of brown algae release pheromones to attract their male mating partners. The biologically active compounds comprise linear or alicyclic unsaturated hydrocarbons derived from the aliphatic terminus of C20 polyunsaturated fatty acids (PUFAs) by oxidative cleavage. The current study addresses the stereochemical course of the pheromone biosynthesis using female gametes of the marine brown alga E. siliculosus and chiral deuterium-labeled arachidonic acids. The biosynthetic sequence is likely to proceed via an intermediary 9-hydroperoxyarachidonic acid, which is cleaved with loss of the C(16)-HR into the C 11-hydrocarbon dictyopterene C and 9-oxonona-(5Z,7E)-dienoic acid.
HIV INTEGRASE INHIBITORS
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Page/Page column 70, (2010/04/28)
Compounds of Formula I are inhibitors of HIV integrase and inhibitors of HIV replication: (I), wherein X1, X2, Y, R1A, R1B, R2 and R3 are defined herein. The compounds are useful for the prophylaxis or treatment of infection by HIV and the prophylaxis, treatment, or delay in the onset or progression of AIDS. The compounds are employed against HIV infection and AIDS as compounds per se (or as hydrates or solvates thereof) or in the form of pharmaceutically acceptable salts. The compounds and their salts can be employed as ingredients in pharmaceutical compositions, optionally in combination with other antivirals, immunomodulators, antibiotics or vaccines.
Stereoselective synthesis of 1,6-dioxaspiro[4.5]decane chiral spiroketal skeleton via C2-symmetric approach using crossmetathesis
Ramu, Errabelli,Rao, B. Venkateswara
, p. 1820 - 1823 (2008/12/22)
A common asymmetric approach for the synthesis of a 1,6-dioxaspiro[4.5]decane chiral spiroketal system, which is a subunit of various natural products, is described and the key aspects of the synthesis are self-crossmetathesis and exploitation of C2
A ring closing metathesis-osmylation approach to oxygenated oxepanes as carbohydrate surrogates
Wong, Jerome C. Y.,Lacombe, Patrick,Sturino, Claudio F.
, p. 8751 - 8754 (2007/10/03)
A ring closing metathesis (RCM)-osmylation sequence has been developed for the formation of highly oxygenated cyclic ethers from the corresponding acyclic dienes. A systematic examination of various substrates in this reaction revealed that the process is general in scope and is insensitive to the number of alkoxy substituents present. Subsequent osmylation of the metathesis product proceeds with excellent diastereoselectivity to furnish highly oxygenated oxepanes. These oxepanes represent one-carbon homologated carbohydrates.
A novel transition metal-catalyzed route to functionalized dihydropyrans and tetrahydrooxepines
Rutjes, Floris P. J. T.,Martijn Kooistra,Hiemstra, Henk,Schoemaker, Hans E.
, p. 192 - 194 (2007/10/03)
A straightforward route for the synthesis of α,α′-disubstituted dihydropyrans and tetrahydrooxepines has been developed involving Pd- and Ru-catalyzed reactions.
Total Synthesis of (10ξ,15R,16S,19S,20S,34R)-Corossoline
Yao, Zhu-Jun,Wu, Yu-Lin
, p. 157 - 160 (2007/10/02)
(10ξ,15R,16S,19S,20S,34R)-Corossoline, a structural representative of the cytotoxic monotetrahydrofuranyl annonaceous acetogenins, was synthesized from two chiral starting materials--(S)-glutamic acid and (R)-ethyl lactate, and 10-undecenoic acid.
