Moriyama, Mizuki published the artcileDivergent asymmetric total synthesis of all four pestalotin diastereomers from (R)-glycidol, Related Products of alcohols-buliding-blocks, the publication is Molecules (2020), 25(2), 394, database is CAplus and MEDLINE.
All four chiral pestalotin diastereomers were synthesized in a straightforward and divergent manner from common (R)-glycidol. Catalytic asym. Mukaiyama aldol reactions of readily-available bis(TMSO)diene (Chan’s diene) with (S)-2-benzyloxyhexanal derived from (R)-glycidol produced a syn-aldol adduct with high diastereoselectivity and enantioselectivity using a Ti(iOPr)4/(S)-BINOL/LiCl catalyst. Diastereoselective Mukaiyama aldol reactions mediated by catalytic achiral Lewis acids directly produced not only a (1’S,6S)-pyrone precursor via the syn-aldol adduct using TiCl4, but also (1’S,6R)-pyrone precursor via the antialdol adduct using ZrCl4, in a stereocomplementary manner. A Hetero-Diels-Alder reaction of similarly available mono(TMSO)diene (Brassard’s diene) with (S)-2-benzyloxyhexanal produced the (1’S,6S)-pyrone precursor promoted by Eu(fod)3 and the (1’S,6R)-pyrone precursor Et2AlCl. Debenzylation of the (1’S,6S)-precursor and the (1’S,6R)-precursor furnished natural (-)-pestalotin (99% ee, 7 steps) and unnatural (+)-epipestalotin (99% ee, 7 steps), resp. Mitsunobu inversions of the obtained (-)-pestalotin and (+)-epipestalotin successfully produced the unnatural (+)-pestalotin (99% ee, 9 steps) and (-)-epipestalotin (99% ee, 9 steps), resp., in a divergent manner. All four of the obtained chiral pestalotin diastereomers possessed high chem. and optical purities (optical rotations, 1H-NMR, 13C-NMR, and HPLC measurements).
Molecules published new progress about 57044-25-4. 57044-25-4 belongs to alcohols-buliding-blocks, auxiliary class Epoxides,Chiral,Aliphatic hydrocarbon chain,Alcohol, name is (R)-Oxiran-2-ylmethanol, and the molecular formula is C3H6O2, Related Products of alcohols-buliding-blocks.
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