Journal ArticleDOI
Practical and efficient approach to the synthesis of guineensine
Shailesh D. Shingala,G. Venkateswar Reddy,R. Sateesh Chandra Kumar,P. Ashok Yadav,K. Suresh Babu +4 more
TLDR
A total synthesis of guineensine, a secondary metabolite of the Piperaceae family, has been executed in 12 steps with an overall yield of 27% and featured novel application of a Julia–Kocienski olefination reaction which effectively constructed alkenamide skeleton.About:
This article is published in Journal of Asian Natural Products Research.The article was published on 2011-01-28. It has received 9 citations till now.read more
Citations
More filters
Journal ArticleDOI
Studies directed towards the total synthesis of koshikalide: stereoselective synthesis of the macrocyclic core
A. Venkanna,Eppakayala Sreedhar,Bandi Siva,Katragadda Suresh Babu,Kothakonda Rajendra Prasad,Janaswamy Madhusudana Rao +5 more
TL;DR: In this article, the synthesis of the macrolactone core of koshikalide is described, starting with readily available 1,4-butanediol and malic acid as synthons, their synthetic strategy involved the reiterative application of Gilman's reaction, Swern oxidation and Sharpless asymmetric epoxidation to establish the required stereocentres.
Journal ArticleDOI
Total Synthesis of the Proposed Structure of Mycobactin J.
TL;DR: The total synthesis of the proposed structure of mycobactin J (MJ), a metabolite of Mycobacterium tuberculosis, is presented and a careful control of the Z-stereochemistry of the unsaturated long chain fatty acid is presented.
Journal ArticleDOI
Novel malyngamide structural analogs: synthesis and biological evaluation
G. Venkateswar Reddy,T. Vijaya Kumar,Bandi Siva,K. Suresh Babu,P. V. Srinivas,P. V. Srinivas,Irum Sehar,A. K. Saxena,J. Madhusudana Rao +8 more
TL;DR: In this paper, a series of novel malyngamide derivatives were synthesized by sharpless asymmetric epoxidation, followed by Julia-Kocinski olefination reactions as key reaction sequence.
Journal ArticleDOI
Total Synthesis of the Endocannabinoid Uptake Inhibitor Guineensine and SAR Studies
Ruben Bartholomäus,Simon Nicolussi,Alice Baumann,Mark Rau,Ana Catarina Simão,Jürg Gertsch,Karl-Heinz Altmann +6 more
TL;DR: A highly efficient total synthesis of guineensine is established, which provided the natural product in only five steps from commercially available 3‐nonyn‐1‐ol in 17 % overall yield, relying on the attachment of the benzodioxolyl moiety to the unsaturated fatty acid chain by means of a Suzuki coupling as the key step.
References
More filters
Journal ArticleDOI
A synthetic method for formyl→ethynyl conversion (RCHO→RCCH or RCCR′)
E. J. Corey,P.L. Fuchs +1 more
Journal ArticleDOI
Phytochemistry of the genus Piper
Virinder S. Parmar,Subhash C. Jain,Kirpal S. Bisht,Rajni Jain,Poonam Taneja,Amitabh Jha,O. D. Tyagi,Ashok K. Prasad,Jesper Wengel,Carl Erik Olsen,Per M. Boll,Per M. Boll +11 more
TL;DR: The secondary metabolites isolated from Piper species for the period 1907 to June 1996 have been reviewed in this paper, where nearly six hundred chemical constituents belonging to different classes of bioactive compounds are listed together with their source(s) and references.
Journal ArticleDOI
A direct synthesis of olefins by reaction of carbonyl compounds with lithio derivatives of 2-[alkyl- or (2'-alkenyl)- or benzyl-sulfonyl]-benzothiazoles
TL;DR: In this article, the lithium alkoxides formed as intermediates undergo an intramolecular addition to the neighboring CN group followed by an S to 0 benzothiazole transfer and simultaneous extrustion of sulfur dioxide and ejection of 2(3H)-benzothiazolone anion.
Journal ArticleDOI
Prostaglandins and congeners. 20. Synthesis of prostaglandins via conjugate addition of lithium trans-1-alkenyltrialkylalanate reagents. A novel reagent for conjugate 1,4-additions
TL;DR: The procedure employed was exactly as previously described as discussed by the authors, and all cases the alcohols isolated were identical with the known compounds by TLC, which are included here for those compounds where they are not in the literature.
Related Papers (5)
A 5C + 5C bicycloaromatization reaction via an aldol condensation cascade. A regioselective synthesis of functionalized naphthalenes from acyclic precursors
D. Stossel,Tak Hang Chan +1 more