Synthesis of epi-oxetin via a serine-derived 2-methyleneoxetane.
The unique reactivity of 2-methyleneoxetanes and 1,5-dioxaspiro[3.2]hexanes has been exploited for the synthesis of epi-oxetin (26), an oxetane-containing beta-amino acid. While the preparation of the natural product oxetin (1) was the original goal, the unexpected diastereoselectivity of an precedented reduction provided the epi-oxetin framework. The methodology described herein should be amenable for the preparation of oxetin with a change in nitrogen protection.
Blauvelt
Marisa L
ML
Department of Chemistry, University of Connecticut, Storrs, Connecticut 06269-3060, USA.
Howell
Amy R
AR
D003500:Cyclization; D004988:Ethers, Cyclic / Q000138:chemical synthesis / Q000737:chemistry*; D008968:Molecular Conformation; D012694:Serine / Q000737:chemistry*; D013237:Stereoisomerism
C527427:2-methyleneoxetane; D004988:Ethers, Cyclic; D012694:Serine; C043272:oxetin