- Isolation, structural elucidation, and absolute stereochemistry of enigmazole a, a cytotoxic phosphomacrolide from the papua new guinea marine sponge cinachyrella enigmatica
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Enigmazole A (1), a novel phosphate-containing macrolide, was isolated from a Papua New Guinea collection of the marine sponge Cinachyrella enigmatica. The structure of 1, including the absolute stereochemistry at all eight chiral centers, was determined by a combination of spectroscopic analyses and a series of microscale chemical derivatization studies. Compound 1 is comprised of an 18-membered phosphomacrolide that contains an embedded exomethylene-substituted tetrahydropyran ring and an acyclic portion that spans an embedded oxazole moiety. Two additional analogues, 15-O-methylenigmazole A and 13-hydroxy-15-O-methylenigmazole A, were also isolated and assigned. The enigmazoles are the first phosphomacrolides from a marine source and 1 exhibited significant cytotoxicity in the NCI 60-cell line antitumor screen, with a mean GI50 of 1.7 μ?.
- Oku, Naoya,Takada, Kentaro,Fuller, Richard W.,Wilson, Jennifer A.,Peach, Megan L.,Pannell, Lewis K.,McMahon, James B.,Gustafson, Kirk R.
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- 3-Methoxybutan-2-one as a sustainable bio-based alternative to chlorinated solvents
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Methylation of acetoin with dimethyl carbonate was performed in a sustainable one-step process, with improved process mass intensity (PMI) and atom economy compared to previously published methods. The resulting product, 3-methoxybutan-2-one (MO) was succ
- Byrne, Fergal P.,Clark, James H.,Hunt, Andrew J.,Jin, Saimeng,McElroy, Con Robert,Quinn, Alex,Sherwood, James
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p. 39412 - 39419
(2021/12/24)
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- Synthesis of β-(Diphenylphosphinoyl) Ketones
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The title compounds may be made by addition of phosphorus nucleophiles (Ph2PO-, Ph2POMgX, Ph2PCl) to enones, by addition of phosphorus-stabilised carbanions to a α-carbonyl cation equivalents (2,3-dichloropropene, epoxides, and α-MeO-ketones) and by oxidation of allyl diphenylphosphine oxides.
- Bell, Andrew,Davidson, Alan H.,Earnshaw, Chris,Norrish, Howard K.,Torr, Richard S.,et al.
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p. 2879 - 2892
(2007/10/02)
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