Synthesis of epothilones via a silicon-tethered RCM reaction.
نویسندگان
چکیده
[reaction: see text] A short synthesis of epothilone B and D is reported. The key step for generating the C12-13-trisubstituted Z-double bond uses a ring-closing metathesis reaction of a disiloxane to form a nine-membered silicon-tethered ring.
منابع مشابه
A highly convergent synthesis of the C1-C31 polyol domain of amphidinol 3 featuring a TST-RCM reaction: confirmation of the revised relative stereochemistry.
The concise enantioselective synthesis of the revised C1-C31 fragment of the polyketide amphidinol 3 was accomplished in 16 steps and 12.8% overall yield. Salient features of the strategy include chemoselective Weinreb amide coupling and concomitant CBS reduction for the preparation of the C1-C15 tris-syn-1,5-diol motif and a temporary silicon-tethered ring-closing metathesis (TST-RCM) reaction...
متن کاملSynthesis, Biological Profiling and Determination of the Tubulin-Bound Conformation of 12-Aza-Epothilones (Azathilones).
12-Aza-epothilones (azathilones) incorporating quinoline side chains and bearing different N12-substituents have been synthesized via highly efficient RCM-based macrocyclizations. Quinoline-based azathilones with the side chain N-atom in the meta-position to the C15 atom in the macrocycle are highly potent inhibitors of cancer cell growth in vitro. In contrast, shifting the quinoline nitrogen t...
متن کاملNano-colloidal silica-tethered polyhedral oligomeric silsesquioxanes with eight branches of 3-aminopropyltriethoxysilane as high performance catalyst for the preparation of furan-2(5H)-ones
An efficient and rapid method for the synthesis of 3,4,5-substituted furan-2 (5H)-ones has been achieved through a three-component reaction of aniline, dialkyl acetylenedicarboxylate, and aromatic aldehydes using nano-colloidal silica-tethered polyhedral oligomeric silsesquioxanes with eight branches of 3-aminopropyltriethoxysilane (nano-colloidal silica @APTPOSS) as a superior catalyst under m...
متن کاملSynthesis of Three - Dimensional Mesoporous Silicon from Rice Husk via SHS Route
Silicon nanoparticles are the focus of attention thanks to their potentialities in advanced applications such as new batteries, photovoltaic cells and so on. The need to porous silicon is thus rising and will follow the same trend. In this work, highly porous nanostructured silicon is synthesized via Self-propagating high-temperature synthesis (SHS) route. Microstructural and phase analyses sho...
متن کاملSynthesis of Dihydrooxepino[3,2-c]Pyrazoles via Claisen Rearrangement and Ring-Closing Metathesis from 4-Allyloxy-1H-pyrazoles.
Synthesis of novel pyrazole-fused heterocycles, i.e., dihydro-1H- or 2H-oxepino[3,2-c]pyrazoles (6 or 7) from 4-allyloxy-1H-pyrazoles (1) via combination of Claisen rearrangement and ring-closing metathesis (RCM) has been achieved. A suitable catalyst for the RCM of 5-allyl-4-allyloxy-1H-pyrazoles (4) was proved to be the Grubbs second generation catalyst (Grubbs2nd) to give the predicted RCM p...
متن کاملذخیره در منابع من
با ذخیره ی این منبع در منابع من، دسترسی به آن را برای استفاده های بعدی آسان تر کنید
برای دانلود متن کامل این مقاله و بیش از 32 میلیون مقاله دیگر ابتدا ثبت نام کنید
ثبت ناماگر عضو سایت هستید لطفا وارد حساب کاربری خود شوید
ورودعنوان ژورنال:
- Organic letters
دوره 7 7 شماره
صفحات -
تاریخ انتشار 2005