A total synthesis of (±)-biotin
- 1 June 1983
- journal article
- research article
- Published by Canadian Science Publishing in Canadian Journal of Chemistry
- Vol. 61 (6) , 1158-1160
- https://doi.org/10.1139/v83-206
Abstract
A total synthesis of (±)-biotin 1 based on the photochemical cycloaddition reaction of 1,3-diacetylimidazolin-2-one 2 with 3,4-dihydro-2-methoxy-2H-pyran 3 is described. The photoadduct 4 was converted into the lactone 6, which bears the complete carbon framework and all the requisite stereochemical features, via hydrolysis, Wittig olefination, and catalytic hydrogenation to the cyclobutanol 5 followed by oxidative rearrangement. Subsequent conversion of the lactone to (±)-biotin followed from literature precedent (5).This publication has 0 references indexed in Scilit: