125637-07-2Relevant articles and documents
Formal total synthesis of (+)-methynolide
Cossy, Janine,Bauer, David,Bellosta, Véronique
, p. 5909 - 5922 (2002)
A formal total synthesis of (+)-methynolide was achieved in 23 steps highlighted by a crotylboration, a ring-closing metathesis, a Sharpless kinetic resolution of an allylic alcohol and a Takai reaction.
Practical Protocols for the Preparation of Highly Enantioenriched Silyl Ethers of (R)-3-Hydroxypentan-2-one, Building Blocks for the Synthesis of Macrolide Antibiotics
Seiple, Ian B.,Hog, Daniel T.,Myers, Andrew G.
, p. 57 - 60 (2016)
Methacrolein is transformed in three steps to (R)-3-tert-butyldiphenylsilyloxypentan-2-one or (R)-3-tert-butyldimethylsilyloxypentan-2-one, compounds which serve as building blocks for the construction of macrolide antibiotics. The route is practical, highly enantioselective, and easily scaled.
Formal total synthesis of (+)-methynolide
Cossy, Janine,Bauer, David,Bellosta, Ve?ronique
, p. 715 - 718 (2002)
A convergent total synthesis of (+)-methynolide was achieved in 23 steps highlighted by a ring-closing metathesis, a Takai reaction, a Sharpless kinetic resolution of an allylic alcohol and a crotylboration.
Ambruticins: tetrahydropyran ring formation and total synthesis
Bowen, James I.,Crump, Matthew P.,Wang, Luoyi,Willis, Christine L.
supporting information, p. 6210 - 6215 (2021/07/28)
The ambruticins are a family of polyketide natural products which exhibit potent antifungal activity. Gene knockout experiments are in accord with the proposal that the tetrahydropyran ring of the ambruticins is formedviathe AmbJ catalysed epoxidation of the unsaturated 3,5-dihydroxy acid, ambruticin J, followed by regioselective cyclisation to ambruticin F. Herein, a convergent approach to the total synthesis of ambruticin J is described as well as model studies involving epoxidation and cyclisations of unsaturated hydroxy esters to give tetrahydropyrans and tetrahydrofurans. The total synthesis involves preparation of three key fragments which were unitedviaa Suzuki-Miyaura cross-coupling and Julia-Kocienski olefination to generate the required carbon framework. Global deprotection to a triol and selective oxidation of the primary alcohol gave, after hydrolysis of the lactone, ambruticin J.
Large-scale preparation of key building blocks for the manufacture of fully synthetic macrolide antibiotics
Hogan, Philip C.,Chen, Chi-Li,Mulvihill, Kristen M.,Lawrence, Jonathan F.,Moorhead, Eric,Rickmeier, Jens,Myers, Andrew G.
, p. 318 - 325 (2018/03/21)
Key building blocks for the production of fully synthetic macrolides have been scaled-up in first time pilot plant and kilo-lab campaigns. These building blocks have supported the discovery of new macrolide antibiotics as well as ongoing preclinical studies.
14-MEMBERED KETOLIDES AND METHODS OF THEIR PREPARATION AND USE
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Paragraph 00591, (2016/05/02)
Provided herein are methods of preparing new 14-membered ketolides via coupling of an eastern and western half moiety, followed by macrocyclization, and optional functionalization. Intermediates in the synthesis of these ketolides including the eastern and western halves are also provided. Pharmaceutical compositions and methods of treating infectious diseases and inflammatory conditions using these ketolides are also provided.
MACROLIDES AND METHODS OF THEIR PREPARATION AND USE
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Paragraph 00675, (2014/10/18)
Provided herein are methods of preparing macrolides by the coupling of an eastern and western half, followed by macrocyclization, to provide macrolides, including both known and novel macrolides. Intermediates in the synthesis of macrolides including the eastern and western halves are also provided. Pharmaceutical compositions and methods of treating infectious diseases and inflammatory conditions using the inventive macrolides are also provided. A general diastereoselective aldol methodology used in the synthesis of the western half is further provided.
Amaranzoles B?F, imidazole-2-carboxy steroids from the marine sponge phorbas amaranthus. C24- N - And C24- O -analogues from a divergent oxidative biosynthesis
Morinaka, Brandon I.,Pawlik, Joseph R.,Molinski, Tadeusz F.
scheme or table, p. 2453 - 2460 (2010/07/17)
Five new steroidal imidazoles, amaranzoles B?F, were isolated from extracts of the marine sponge Phorbas amaranthus along with the known amaranzole A. The C24-N-(4-p-hydroxyphenyl)imidazol-5-yl constitution found in amaranzoles A, C, and D is replaced by a C24-O-(4-p-hydroxyphenyl)imidazole-2-carboxylate motif in amaranzoles B, E, and F. The structures were elucidated by interpretation of spectroscopic data. The C24 side chain configuration was assigned by synthesis of a model ester followed by chiroptical comparisons of its CD spectrum with that of an amaranzole B derivative.
Enantioselective synthesis of allylic alcohols via an oxazaborolidinium ion catalyzed diels-alder/retro-diels-alder sequence
Jones, Simon,Valette, Damien
supporting information; experimental part, p. 5358 - 5361 (2010/01/19)
A triflimide-activated oxazaborolidine catalyst successfully promoted the asymmetric Diels-Alder reaction of 9-methylanthracene with methacrolein in high regio- and enantioselectivity. The cycloadduct obtained was subsequently used as a chiral template to
Total synthesis of jerangolid D
Pospisil, Jiri,Marko, Istvan E.
, p. 3516 - 3517 (2008/01/01)
A short and convergent synthesis of jerangolid D is described. As key steps, a Blaise reaction is employed to construct the lactone ring, a diastereoselective multicomponent Sakurai condensation leads to the dihydropyran ring, and the skipped diene is ass
