Enantioselective formal total synthesis of (−)-trachyspic acid
✍ Scribed by Frederick Calo; Jeffery Richardson; Andrew J.P. White; Anthony G.M. Barrett
- Publisher
- Elsevier Science
- Year
- 2009
- Tongue
- French
- Weight
- 428 KB
- Volume
- 50
- Category
- Article
- ISSN
- 0040-4039
No coin nor oath required. For personal study only.
✦ Synopsis
An enantioselective formal total synthesis of (À)-trachyspic acid was carried out using, as key steps, an asymmetric aldol reaction of a chiral oxazolidinone and a diastereoselective alkylation of a chiral 1,3dioxolan-2-one. The key lactone 3 was synthesized in five steps starting from dioxolanone 9.
📜 SIMILAR VOLUMES
Aldol reaction of di-tert-butyl 4-(4-methoxybenzyloxy)-2-oxobutanoate with pent-4-enal using (S)-1-(3,5-bis(trifluoromethyl)phenyl)-3-(pyrrolidin-2-ylmethyl)thiourea hydrochloride as a catalyst, followed by Pinnick oxidation and tert-butyl esterification, gave (2S,3S)-di-tert-butyl 2-(2-(4-methoxybe