81997-76-4Relevant articles and documents
Enantioselective divergent syntheses of several polyhalogenated plocamium monoterpenes and evaluation of their selectivity for solid tumors
Vogel, Carl V.,Pietraszkiewicz, Halina,Sabry, Omar M.,Gerwick, William H.,Valeriote, Frederick A.,Vanderwal, Christopher D.
, p. 12205 - 12209 (2014)
The family of polyhalogenated monoterpenes from Plocamium counts over a hundred known members. Using glyceraldehyde acetonide as a chiral-pool precursor, an enantioselective and divergent strategy was developed that provides a blueprint for the synthesis of many of the small yet complex acyclic members of this family. The broad applicability of this approach is demonstrated with the short, eight-step synthesis of four natural products and three analogues. These syntheses are the first of any members of the acyclic polyhalogenated Plocamium monoterpenes and permitted the evaluation of their selectivity against a range of tumor cell lines. Glyceraldehyde acetonide serves as a chiral glyoxal equivalent and a linchpin for the enantioselective synthesis of several acyclic polyhalogenated monoterpenes from the red algae Plocamium. Several of these compounds demonstrate selective toxicity towards solid-tumor cell lines over leukemia cell lines, as well as low-micromolar cytotoxicity towards the HCT-116 human colon carcinoma cell line.
Preparation method of 2-C-methyl-4, 5-O-(1-methylvinyl)-D-arabitic acid ethyl ester
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Paragraph 0039-0048, (2019/01/24)
The invention discloses a preparation method of 2-C-methyl-4, 5-O-(1-methylvinyl)-D-arabitic acid ethyl ester (formula I). Compared with the prior art, the preparation method has short reaction steps,reduces the use of organic solvents and generation of solid waste. At the same time, the used reagents are all conventional reagents, the method has the characteristics of simple operation, mild reaction conditions and environmental friendliness, and can achieve industrial preparation of 2-C-methyl-4, 5-O-(1-methylvinyl)-D-arabitic acid ethyl ester.
A Synthesis of (-)-(R)- and (+)-(S)-Lavandulol, (+)-Lavandulyl 2-methylbutanoate, and (+)-lavandulyl senecioate through orthoester johnson-claisen rearrangement
Fernandes, Rodney A.,Chowdhury, Asim K.
, p. 5165 - 5170 (2013/11/06)
An efficient synthesis of (-)-(R)- and (+)-(S)-lavandulol, (+)-lavandulyl 2-methylbutanoate and (+)-lavandulyl senecioate is presented in this paper. The synthetic strategy features a chiral-pool approach to an allyl alcohol intermediate, and an orthoester Johnson-Claisen rearrangement as the key step. An efficient synthesis of (-)-(R)- and (+)-(S)-lavandulol, (+)-lavandulyl 2-methylbutanoate and (+)-lavandulyl senecioate is presented. The synthetic strategy features a chiral-pool approach to an allyl alcohol intermediate, and an orthoester Johnson-Claisen rearrangement as the key step. Copyright