Obolactone

Obolactone 구조식 이미지
카스 번호:
712272-88-3
상품명:
Obolactone
동의어(영문):
Obolactone;(6R)-6-[[(2R)-3,4-Dihydro-4-oxo-6-[(1E)-2-phenylethenyl]-2H-pyran-2-yl]methyl]-5,6-dihydro-2H-pyran-2-one;2H-Pyran-2-one, 6-[[(2R)-3,4-dihydro-4-oxo-6-[(1E)-2-phenylethenyl]-2H-pyran-2-yl]methyl]-5,6-dihydro-, (6R)-
CBNumber:
CB92725441
분자식:
C19H18O4
포뮬러 무게:
310.34
MOL 파일:
712272-88-3.mol

Obolactone 속성

녹는점
116-118℃
끓는 점
522.2±49.0 °C(Predicted)
밀도
1.270±0.06 g/cm3(Predicted)

안전

Obolactone C화학적 특성, 용도, 생산

Synthesis

The synthesis of (+)-obolactone (14, Scheme 3) by Brückner and Walleser employed the same conditions from the synthesis of 17-deoxyroflamycoin to transform bis-epoxide R,R-4 to bis-homoallylic diol S,S-8.  Diol 8 was then protected using 2,2-dimethoxypropane under acidic conditions to provide acetonide 12 in 95% yield. One of the alkene functional groups of the C2- symmetric acetal underwent a subsequent symmetry-breaking Wacker oxidation. Treatment of acetonide 12 with catalytic PdCl2 under an atmosphere of oxygen using CuCl as the stoichiometric oxidant afforded a 64% yield of methyl ketone 13, with over-oxidation to the diketone also observed (18% yield). The methyl ketone functionality of 13 was critical for the installation of the dihydro-g-pyranone moiety in the natural product, while the syn-orientation of the C–O bonds was achieved through Mitsunobu inversion of the lactone stereocenter. Brückner and Walleser specifically mention that while Krische and co-workers have reported on an impressive single-step procedure for the catalytic enantioselective synthesis of bishomoallylic diol (S,S-4) from 1,3-propanediol, and have used this method extensively in the synthesis of polyketide natural products, 21,22 the high cost of catalyst and ligand precluded their use on scale in this case.
(+)-obolactone synthesis

Obolactone 준비 용품 및 원자재

원자재

준비 용품


Obolactone 공급 업체

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