mardi 31 juillet 2007

Neooxazolomycin (Part1)


Onyango, Tsurumoto, Imai, Takahashi, Ishihara, Hatakeyama. ACIEE, 2007, Early View, DOI: 10.1002/anie.200702229

Neooxazolomycin was isolated by Uemura in 1985, together with the oxazolomycin, this oxazole polyene lactam-lactone antibiotics was synthesized first by Kende in 1990.

But I find interesting the way to achieve the synthesis of the furo-pyrrole moiety (lactam-lactone) by Hatakeyama. This synthesis, I present you, starts from the reaction of heptynol (see below) and tetramethyldisilazane ((HMe2Si)2NH) provides hydromethylsilylether (not shown) which upon treatment with Pt(dvds) as catalyst in THF gives the cyclic siloxane. After iodination with I2 in presence of CsF in a DMF/MeOH mixture, the iodoalkenol is obtained in 82% (3 steps). The synthesis continues with the oxidation of the alcohol under Jones conditions, and the carboxylic acid is condensed with 2-(methylamino)malonate through the acid chloride to provide the amide in 62% Yield (3 steps). The cyclization of the alkenyl amide with the Pd(OAc)2/PPh3 couple, K2CO3 and nBu4NBr in solution in DMF results in the formation of the alkylidene-pyrrolidinone in 84% yield. The crucial step is undoubtedly the stereoselective dihydroxylation using OsO4/NMO with a concomitant lactonization to furnish lactam-lactone moiety in 88% yield.


A very interersting paper with a lot of different chemistry: Reformatsky, Stille, Nozaki-Hiyama-Kishi, Tamao hydrosilylation, Dihydroxylation.

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Hello Everybody,
My name is Mrs Sharon Sim. I live in Singapore and i am a happy woman today? and i told my self that any lender that rescue my family from our poor situation, i will refer any person that is looking for loan to him, he gave me happiness to me and my family, i was in need of a loan of S$250,000.00 to start my life all over as i am a single mother with 3 kids I met this honest and GOD fearing man loan lender that help me with a loan of S$250,000.00 SG. Dollar, he is a GOD fearing man, if you are in need of loan and you will pay back the loan please contact him tell him that is Mrs Sharon, that refer you to him. contact Dr Purva Pius,via email:(urgentloan22@gmail.com) Thank you.

BORROWERS APPLICATION DETAILS


1. Name Of Applicant in Full:……..
2. Telephone Numbers:……….
3. Address and Location:…….
4. Amount in request………..
5. Repayment Period:………..
6. Purpose Of Loan………….
7. country…………………
8. phone…………………..
9. occupation………………
10.age/sex…………………
11.Monthly Income…………..
12.Email……………..

Regards.
Managements
Email Kindly Contact: urgentloan22@gmail.com

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