Abstract
A formal total synthesis of (±)-amathaspiramide F through a tandem palladium-catalyzed allylic amination/[2,3]-Stevens rearrangement is reported. The unexpected diastereoselectivity of the [2,3]-Stevens rearrangement was controlled by the substitution patterns of an aromatic ring. This discovery represents a new stereocontrolling element for [2,3]-sigmatropic rearrangements in complex molecular settings.
Original language | English (US) |
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Pages (from-to) | 5138-5141 |
Number of pages | 4 |
Journal | Organic Letters |
Volume | 15 |
Issue number | 19 |
DOIs | |
State | Published - Oct 4 2013 |
ASJC Scopus subject areas
- Biochemistry
- Physical and Theoretical Chemistry
- Organic Chemistry