A short and practical synthesis of two Hagen’s gland lactones |
| |
Authors: | Evelyn Paz-Morales |
| |
Institution: | Centro de Investigación de la Facultad de Ciencias Químicas, BUAP. 14 Sur Esq. San Claudio, San Manuel, 72570 Puebla, Mexico |
| |
Abstract: | A seven-step total synthesis of Hagen’s gland lactones 1 and 2 starting from 1,2-O-isopropylidene-α-d-xylofuranose 3 is reported. The success of this short and practical synthesis depends on the use of two key reactions: a stereoselective nucleophilic substitution at the anomeric position of 5 and 6, which allowed the construction of the γ-lactone ring, and an alkyl substitution reaction on tosylated compound 4, which permitted the carbon chain elongation of the tetrahydrofuran ring appendage at C-6. |
| |
Keywords: | Hagen&rsquo s gland lactones Oxocarbenium ion Nucleophilic substitution Woerpel&rsquo s model |
本文献已被 ScienceDirect 等数据库收录! |
|