Recent Applications of Ammonium Ylide Based [2,3]-Sigmatropic and [1,2]-Stevens Rearrangements To Transform Amines into Natural Products

Zachary Schwartz; Chelsea Valiton; Myles Lovasz; Andrew G. Roberts

doi:10.1055/s-0042-1751446

Synthesis, Table of Contents

Synthesis 2024; 56(01): 87-106
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

Zachary Schwartz‡

,

Chelsea Valiton‡

,

Myles Lovasz‡

,

Andrew G. Roberts ∗

Abstract

All articles of this category

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 - alkaloids

Full Text

References

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