Stereoselective approach to alk-2-yne-1,4-diols. Application to the synthesis of musclide B

✍ Scribed by Marta Amador; Xavier Ariza; Jordi Garcia; Jordi Ortiz

• Book ID: 104250818
• Publisher: Elsevier Science
• Year: 2002
• Tongue: French
• Weight: 130 KB
• Volume: 43
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(02)00395-7

✦ Synopsis

An expedient method for the stereoselective preparation of alk-2-yne-1,4-diols has been achieved, based on the addition of chiral alk-1-yn-3-ols (or their protected derivatives) to aldehydes mediated by zinc triflate, Et 3 N, and (+)-or (-)-Nmethylephedrine. In general, the configuration observed at the emergent stereocenter depends on the N-methylephedrine employed resulting in good to excellent diastereoselectivities. This strategy has been applied to the enantioselective synthesis of musclide B, a bioactive metabolite from musk.