Stereocontrolled Synthesis of 2-Deoxy-galactopyranosides via Isopropylidene-Protected 6- O-Silylated Donors.
Sign Up to like & getrecommendations! Published in 2018 at "Organic letters"
DOI: 10.1021/acs.orglett.8b00632
Abstract: The stereocontrolled synthesis of 2-deoxy-d- arabino-hexopyranosides ("galactopyranosides") using 3,4- O-isopropylidene-6- O- tert-butyldiphenylsilyl-protected glycosyl donors is reported. 2-Deoxy-thioglycoside 3e gives excellent α-selectivity, while galactal 9 leads to, in a two-step protocol, 2-deoxy-β-glycosides in high stereoselectivity. The… read more here.
Keywords: synthesis deoxy; deoxy galactopyranosides; isopropylidene; deoxy ... See more keywords
Stereocontrolled Synthesis of (±)-Melokhanine E via an Intramolecular Formal [3 + 2] Cycloaddition.
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DOI: 10.1021/acs.orglett.9b04546
Abstract: A convergent sequence to access the indole alkaloid (±)-melokhanine E in 12-steps (8-step longest linear sequence) and an 11% overall yield is reported. The approach utilizes two cyclopropane moieties as reactive precursors to a 1,3-dipole… read more here.
Keywords: synthesis melokhanine; formal cycloaddition; melokhanine; melokhanine via ... See more keywords
Stereocontrolled Synthesis of the Fully Glycosylated Monomeric Unit of Lomaiviticin A.
Sign Up to like & getrecommendations! Published in 2022 at "Journal of the American Chemical Society"
DOI: 10.1021/jacs.2c07631
Abstract: We describe a stereocontrolled synthesis of 3, the fully glycosylated monomeric unit of the dimeric cytotoxic bacterial metabolite (-)-lomaiviticin A (2). A novel strategy involving convergent, site- and stereoselective coupling of the β,γ-unsaturated ketone 6… read more here.
Keywords: glycosylated monomeric; stereocontrolled synthesis; synthesis; fully glycosylated ... See more keywords
Stereocontrolled Synthesis of Kalihinol C.
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DOI: 10.1021/jacs.7b01124
Abstract: We report a concise chemical synthesis of kalihinol C via a possible biosynthetic intermediate, "protokalihinol", which was targeted as a scaffold en route to antiplasmodial analogs. High stereocontrol of the kalihinol framework relies on a… read more here.
Keywords: kalihinol; stereocontrolled synthesis; synthesis kalihinol;
P-stereocontrolled synthesis of oligo(nucleoside N3′→O5′ phosphoramidothioate)s – opportunities and limitations
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DOI: 10.1039/d0ra04987e
Abstract: 3′-N-(2-Thio-1,3,2-oxathiaphospholane) derivatives of 5′-O-DMT-3′-amino-2′,3′-dideoxy-ribonucleosides (NOTP-N), that bear a 4,4-unsubstituted, 4,4-dimethyl, or 4,4-pentamethylene substituted oxathiaphospholane ring, were synthesized. Within these three series, NOTP-N differed by canonical nucleobases (i.e., AdeBz, CytBz, GuaiBu, or Thy). The monomers were… read more here.
Keywords: phosphoramidothioate; synthesis oligo; oligo nucleoside; phosphoramidothioate opportunities ... See more keywords
Concise Stereocontrolled Synthesis of an α-Carbagalactose Segment of RCAI-56, a Candidate Anticancer Agent
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DOI: 10.1055/s-0037-1611806
Abstract: RCAI-56 is a synthetic glycolipid exhibiting a potent antitumor activity by stimulation of natural killer T cells. Tetra-O-benzyl-α-carbagalactose, an important synthetic segment of RCAI-56, was stereoselectively synthesized from 1,4-dichloro-2-butene in nine steps, including the key… read more here.
Keywords: stereocontrolled synthesis; rcai; concise stereocontrolled; segment rcai ... See more keywords