187745-66-0Relevant academic research and scientific papers
Total synthesis of (-)-ulapualide A, a novel tris-oxazole macrolide from marine nudibranchs, based on some biosynthesis speculation
Pattenden, Gerald,Ashweek, Neil J.,Baker-Glenn, Charles A. G.,Kempson, James,Walker, Gary M.,Yee, James G. K.
supporting information; experimental part, p. 1478 - 1497 (2008/10/09)
A new, second generation, total synthesis of ulapualide A (1), whose stereochemistry was recently determined from X-ray analysis of its complex with the protein actin, is described. The synthesis is designed and based on some speculation of the biosynthet
A convergent total synthesis of (-)-mucocin: An acetogenin from Annonaceae
Hoppen, Sabine,Baeurle, Stefan,Koert, Ulrich
, p. 2382 - 2396 (2007/10/03)
A total synthesis of the Annonaceous acetogenin mucocin has been accomplished. The synthesis follows a convergent strategy, wherein at a very late stage the left part of the molecule is connected with the right part. The key reaction is the stereocontrolled addition of an organomagnesium compound 2 to the aldehyde 3. The THP ring of mucocin is build by a 6-endo epoxide cyclization of an epoxyacetonide precursor (16 → 17). The new modular synthetic approach developed herein should be useful for the synthesis of other related natural products as well as pharmacologically interesting analogues.
Total synthesis of (-)-mucocin
Baeurle, Stefan,Hoppen, Sabine,Koert, Ulrich
, p. 1263 - 1266 (2007/10/03)
A highly convergent, modular strategy for the total synthesis of the annonaceous acetogenin (-)-mucocin is reported. The remarkable features are the endoselective formation of the tetrahydropyran ring from an activated epoxide and the stability of the but
Total synthesis of the piperidinol alkaloid (-)-(2R,3R,6S)-cassine
Oetting, Joerg,Holzkamp, Jens,Meyer, Hartmut H.,Pahl, Axel
, p. 477 - 484 (2007/10/03)
A highly efficient, flexible and diastereoselective route to all-cis-2,6-disubstituted 3-piperidinols has been accomplished. The key component of the synthesis is a chiral β-hydroxyester, which was obtained by lipase catalyzed kinetic resolution. Based on this starting material, diastereoselective alkylation of its dianion, Curtius rearrangement to a 2-oxazolidinone, Grignard reaction to introduce the side-chain and conversion of the aliphatic 2-oxazolidinone into a 3-piperidinol by imine cyclization lead to the exemplary total synthesis of naturally occurring (-)-(2R,3R,6S)-cassine.
