TY - JOUR
T1 - Stereoselective Alkylation of the Vinylketene Silyl N,O-Acetal and Its Application to the Synthesis of Mycocerosic Acid
AU - Nakamura, Tatsuya
AU - Kubota, Kei
AU - Ieki, Takanori
AU - Hosokawa, Seijiro
N1 - Publisher Copyright:
© 2015 American Chemical Society.
PY - 2016/1/4
Y1 - 2016/1/4
N2 - Stereoselective alkylation of the vinylketene silyl N,O-acetal possessing a chiral auxiliary has been achieved by using activated alkyl halides including allyl iodides, benzyl iodides, and propargyl iodide with Ag(I) ion in the presence of BF3·OEt2. The reaction proceeded to give reduced polyketides in high stereoselectivity. The synthesis of mycocerosic acid, a component of the cell envelope of Mycobacterium tuberculosis, has been accomplished by this methodology. During the synthetic studies, 2-methylbenzimidazole was found to be a bulky proton source which worked in the presence of liquid ammonia.
AB - Stereoselective alkylation of the vinylketene silyl N,O-acetal possessing a chiral auxiliary has been achieved by using activated alkyl halides including allyl iodides, benzyl iodides, and propargyl iodide with Ag(I) ion in the presence of BF3·OEt2. The reaction proceeded to give reduced polyketides in high stereoselectivity. The synthesis of mycocerosic acid, a component of the cell envelope of Mycobacterium tuberculosis, has been accomplished by this methodology. During the synthetic studies, 2-methylbenzimidazole was found to be a bulky proton source which worked in the presence of liquid ammonia.
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U2 - 10.1021/acs.orglett.5b03422
DO - 10.1021/acs.orglett.5b03422
M3 - Article
C2 - 26673532
AN - SCOPUS:84953376032
SN - 1523-7060
VL - 18
SP - 132
EP - 135
JO - Organic Letters
JF - Organic Letters
IS - 1
ER -