Journal
TETRAHEDRON
Volume 74, Issue 10, Pages 1059-1070Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2018.01.035
Keywords
Divergent synthesis; Oxonium ylide; Rearrangement; Rhodium; Lactonization
Categories
Funding
- Japan Society for the Promotion of Science (JSPS) [JP16K08158]
- JSPS Core-to-Core Program, B. Asia-Africa Science Platforms
- Grants-in-Aid for Scientific Research [16K08158] Funding Source: KAKEN
Ask authors/readers for more resources
In this study, we described the divergent synthesis of (+)-tanikolide and its analogues, such as (4S)- and (4R)-hydroxytanikolides, and nortanikolide, employing a stereoselective dirhodium(II)-catalyzed reaction to construct the quaternary chiral center of tanokolides. The key steps involve (a) a dirhodium(II)-catalyzed oxonium ylide formation-[2,3]-sigmatropic rearrangement, (b) an N-heterocyclic carbene-catalyzed ring-expansion lactonization of tetrahydrofurfural, or (c) an oxidative cleavage of tetrahy-drofuran-5-methanol to gamma-lactone using a 2-iodobenzamide catalyst. This route would provide high flexibility for analogue synthesis because the long side chain can be introduced at a later stage in the synthesis. (C) 2018 Elsevier Ltd. All rights reserved.
Authors
I am an author on this paper
Click your name to claim this paper and add it to your profile.
Reviews
Recommended
No Data Available