Seebach, Dieter; Maestro, Miguel A.; Sefkow, Michael; Adam, Geo; Hintermann, Samuel; Neidlein, Axel published the artcile< Total synthesis of Myxovirescins. 1. Strategy and construction of the ""southeastern"" part [O(1)-C(14)]>, Safety of (9Z,12Z)-Methyl octadeca-9,12-dienoate, the main research area is myxovirescin total synthesis.
In this and the following two papers the synthesis of myxovirescins A1, A2 and M2, 28-membered macrocyclic lactam-lactones with antibiotic activity, is described. A retrosynthetic anal. of the myxovirescin family of ca. 30 target mols. leads to a strategy which could be applied to approx. half of them by slight variations of the building blocks used. The southeastern part of the mol., containing the atoms O(1)-C(14) of myxovirescins A and M is described in this first paper. The assembly is achieved by using the following appropriately protected units: (S)-2-hydroxy-pentanoic acid, ([1,3]dithian-2-ylmethyl)-amine, the triflate of (S,R)-2,2-dimethyl-5-vinyl-[1,3]dioxolan-4-ylmethanol, (E)-3-bromo-2-buten-1-ol, and (E)-2-bromo-2-buten-1,4-diol, the starting materials for these being malic acid, aminoacetaldehyde, ribose, crotyl alc. and butyne-1,4-diol. The building blocks are put together by using the following key steps: Kolbe electrolysis, amide formation, lithiodithiane alkylation, and Suzuki coupling. The only newly created chirality center [C(6) of the target mols.] is generated stereoselectively by a Li-selectride reduction/Mitsunobu inversion. The termini of the O(1)-C(14) fragment, I (X = H, OMe), carry a (protected) hydroxy acid and an aldehyde group for the Julia coupling and lactonization, resp., in the final steps of the synthesis. All intermediates are fully characterized. The x-ray crystal structures of two compounds prepared for incorporation as N(4)-C(11) and as C(12)-C(14) of the target mols. are also described.
Liebigs Annalen der Chemie published new progress about 112-63-0. 112-63-0 belongs to class esters-buliding-blocks, and the molecular formula is C19H34O2, Safety of (9Z,12Z)-Methyl octadeca-9,12-dienoate.
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Ester – Wikipedia,
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