By Yong Zhou
Nomenclature of standard Single-Strand natural Polymers discusses the elemental rules and the elemental principles of the structure-based nomenclature. This ebook comprises targeted extensions and purposes of those ideas and ideas to single-strand natural polymers. An Appendix is integrated containing a proscribing record of appropriate source-based names, in addition to the corresponding structure-based names, of universal polymers.
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Extra info for Nomenclature of Regular Single-Strand Organic Polymers. Commission on Macromolecular Nomenclature
Protection of the alcohol and displacement of the halogen with acetylide ion then gave a 98% yield of 164. Syn addition of tributyltin hydride proceeded in 94% yield via a radical chain mechanism to give olefin 165, whose 2-geometry is to become the A10711 double bond. Metalation and formation of the cuprate 166 then set the stage for construction of the cyclopentane ring. O]hexene 167 was hydroborated and oxidized to afford anti alcohol 168 in up to 80% yield. Chromic acid oxidation of 168 was followed by p elimination of malonate anion with Et,N to produce enone 169 (86%).
The use of this complex oxidizing reagent permitted for the facile deprotection to the natural product, a step that eluded Hase. There was no report of the formation of the anti diastereomer; however, the low isolated yield and information provided by Trost5* about a similar oxidation (vide infra) suggests that the anti isomer was probably formed. Acidic desilylethylation then provided synthetic 1. I ) TMSCI, E t 3 N 2) Pb(02CCH2CH$02CH2CH2TMS), !? 3. Takei's A26771B synthesis. 4). The addition of a-lithio ethyl vinyl ether and acylation of the resulting alcohol gave allylic acetate 34.
Chromatographic separation of the p-isomer then provided 48. 7. Masamune's methymycin synthesis. 7) was converted in a straightforward manner to the aldehyde 81. Ketal cleavage and acetylation then gave the C-8 to C-1 1 nucleophilic fragment 63 (96%). As in the Masamune synthesis, construction of the C-7 fragment began with a Prelog-Djerassi lactone analog. Accordingly, compound 64, the methyl ester of 52, was selectively hydrolyzed and reesterified to the methyl benzyl diester. The remaining hydroxyl group was protected as the chloroacetate to give 65 in The Total Synthesis of Macrocyclic Lactones 50 87% yield.