959775-11-2Relevant academic research and scientific papers
RCM mediated synthesis of macrosphelides I and G
Sharma, Gangavaram V.M.,Veera Babu, Kagita
, p. 2175 - 2184 (2008/02/11)
The total synthesis of 16-membered macrolides, macraosphelides I and G, has been achieved starting from ethyl-(S)-lactate and (S)-malic acid. A combination of Jacobsen's hydrolytic kinetic resolution and Sharpless epoxidation is used for the creation of two stereogenic centres, while Yamaguchi esterification and ring-closing metathesis strategies were used for the construction of the lactone ring.
Enantioselective synthesis of a putative hexaketide intermediate in the biosynthesis of the squalestatins
Simpson, Thomas J.,Smith, Robert W.,Westaway, Susan M.,Willis, Christine L.,Buss, Antony D.,Cannell, Richard J. P.,Dawson, Michael J.,Rudd, Brian A. M.
, p. 5367 - 5370 (2007/10/03)
A convergent synthesis of (3R, 5Z, 8E, 10R)-3-hydroxy-8,10-dimethyl-11-phenylundec-5,8-dienoic acid 4, a putative hexaketide intermediate in the biosynthesis of the squalestatins, is described. A key step in the assembly of the carbon framework is the coupling of alkyne 19 with allylic bromide 13 giving, after further functional group manipulations, the target compound as a single diastereomer. The approach may be adapted for the preparation of the corresponding (3S, 5Z, 8E, 10R)-isomer as well as for the incorporation of carbon-13 labels required for biosynthetic studies.
