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Synthesis 2024; 56(01): 87-106
DOI: 10.1055/s-0042-1751446
DOI: 10.1055/s-0042-1751446
special topic
Advances in Skeletal Editing and Rearrangement Reactions
Recent Applications of Ammonium Ylide Based [2,3]-Sigmatropic and [1,2]-Stevens Rearrangements To Transform Amines into Natural Products
We are grateful for financial support from the University of Utah Department of Chemistry and the Donors of the American Chemical Society Petroleum Research Fund (ACS PRF 62220-DNI1).
Abstract
Ammonium ylide based [2,3]-sigmatropic and [1,2]-Stevens rearrangements enable the transformation of tertiary amines into rearranged and functionalized intermediates en route to many polycyclic natural product targets. Herein, we summarize recent applications of these rearrangement reactions in formal and total synthesis endeavors while highlighting innovative improvements to these transforms.
1 Introduction
2 Ammonium Ylide Based [2,3]-Sigmatropic Rearrangements in Natural Product Synthesis
2.1 (–)-Cephalotaxine
2.2 (±)-Amathaspiramide F
2.3 (–)-Cephalezomine G and Its C3 Epimer
2.4 (±)-Strictamine
2.5 (–)-Doxycycline
3 [1,2]-Stevens Rearrangements Toward Natural Products
3.1 Ring-Expanding [1,2]-Stevens Rearrangements en route to (±)-Tylophorine, (±)-7-Methoxycryptopleurine, and (±)-Xylopinine
3.2 Enantioselective Synthesis of Iboga Alkaloids and (+)-Vinblastine
4 Selected Methodology
4.1 Ammonium Ylide Based [2,3]-Sigmatropic Rearrangements To Form Natural Product Cores
4.2 Cascade Reactions Involving [1,2]-Stevens Rearrangement/ Hofmann-Type Elimination Events
5 Conclusions
Key words
ammonium ylides - [1,2]-Stevens rearrangement - [2,3]-sigmatropic rearrangement - [2,3]-Stevens rearrangement - natural products - alkaloidsPublication History
Received: 05 February 2023
Accepted after revision: 23 March 2023
Article published online:
04 May 2023
© 2023. Thieme. All rights reserved
Georg Thieme Verlag KG
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