https://pubs.rsc.org/en/content/articlepdf/2019/NP/C8NP00092A

Marine natural products.

1. Molecular Formulas and What Can Be Learned from Them. 2. Infrared Spectroscopy. 3. Nuclear Magnetic Resonance Spectroscopy Part One: Basic Concepts. 4. Nuclear Magnetic Resonance Spectroscopy Part Two: Carbon-13 Spectra, Including Heteronuclear Coupling with Other Nuclei. 5. Nuclear Magnetic Resonance Spectroscopy Part Three: Spin-Spin Coupling. 6. Nuclear Magnetic Resonance Spectroscopy Part Four: Other Topics in One-Dimensional NMR. 7. Ultraviolet Spectroscopy. 8. Mass Spectrometry. 9. Combined Structure Problems. 10. Nuclear Magnetic Resonance Spectroscopy Part Five: Advanced NMR Techniques. Answers to Selected Problems. Appendix 1: Infrared Absorption Frequencies of Functional Groups. Appendix 2: Some Representative Chemical Shift Values for Various Types of Protons. Appendix 3: Typical Proton Coupling Constants. Appendix 4: Calculation of Proton (1H) Chemical Shifts. Appendix 5: Calculation of Carbon-13 Chemical Shifts. Appendix 6: 13C Coupling Constants. Appendix 7: Tables of Precise Masses and Isotopic Abundance Ratios for Molecular Ions Under Mass 100 Containing Carbon, Hydrogen, Nitrogen, and Oxygen. Appendix 8: Common Fragment Ions Under Mass 105. Appendix 9: Handy-Dandy Guide to Mass Spectral Fragmentation Patterns. Appendix 10: Index of Spectra.

Introduction to Spectroscopy

Recent advances in olefin metathesis and its application in organic synthesis

Since the discovery of organic azides by Peter Griess more than 140 years ago, numerous syntheses of these energy-rich molecules have been developed. In more recent times in particular, completely new perspectives have been developed for their use in peptide chemistry, combinatorial chemistry, and heterocyclic synthesis. Organic azides have assumed an important position at the interface between chemistry, biology, medicine, and materials science. In this Review, the fundamental characteristics of azide chemistry and current developments are presented. The focus will be placed on cycloadditions (Huisgen reaction), aza ylide chemistry, and the synthesis of heterocycles. Further reactions such as the aza-Wittig reaction, the Sundberg rearrangement, the Staudinger ligation, the Boyer and Boyer-Aube rearrangements, the Curtius rearrangement, the Schmidt rearrangement, and the Hemetsberger rearrangement bear witness to the versatility of modern azide chemistry.

Organic Azides: An Exploding Diversity of a Unique Class of Compounds

The advent of well-defined catalysts for olefin metathesis which combine high activity, durability, and excellent tolerance towards polar functional groups has revolutionized the field. The past decade has seen the rapid embrace of these reagents as tools for advanced organic and polymer chemistry and the success of this development is witnessed by a plethora of elegant applications to the synthesis of natural and nonnatural products. This review article provides an overview of these developments and intends to familiarize the reader with some very recent advances which hold the promise to expand the scope of the reaction even further. Moreover, the positive impact of metathesis on the fundamental logic of retrosynthetic planning is demonstrated by means of typical examples. Finally, it will be shown that metathesis is by no means restricted to alkenes as substrates, and some comments on metathesis reactions following unconventional mechanistic pathways will also be presented.

Olefin Metathesis and Beyond

Syntheses via Vinyl Sulfones. Part 62. Triflone Chemistry. Part 4. Stereo- and Regiospecific Syntheses of α- and β-Substituted Vinyl and Dienyl Triflones via the Stille Reaction.

Syntheses via Vinyl Sulfones. Part 66. Palladium(0)‐Mediated Aminospirocyclization of Tertiary Allylic Sulfones. Stereospecific Construction of the Azabicyclic Ring System of Cephalotaxine.

Regiospecific 4,6-Functionalization of Pyranosides via Dimethylboron Bromide-Mediated Cleavage of Phthalide Ortho Esters.

Inexpensive enantiopure (+)-limonene oxide 1 is converted to 4-(R)-(t-butyldimethylsilyloxy)-cyclohex-2-en-1-one 2a . All isolated intermediates can be distilled obviating the need for chromatography. With 2a,b in hand, a formal synthesis of (±)-mesembranol 17 using vinyl triflate methodology is high yielding.

Philip L. Fuchs

Papers

Syntheses via Vinyl Sulfones. Part 62. Triflone Chemistry. Part 4. Stereo- and Regiospecific Syntheses of α- and β-Substituted Vinyl and Dienyl Triflones via the Stille Reaction.

Syntheses via Vinyl Sulfones. Part 66. Palladium(0)‐Mediated Aminospirocyclization of Tertiary Allylic Sulfones. Stereospecific Construction of the Azabicyclic Ring System of Cephalotaxine.

Regiospecific 4,6-Functionalization of Pyranosides via Dimethylboron Bromide-Mediated Cleavage of Phthalide Ortho Esters.

An Efficient and Convenient Synthesis of Enantiopure 4-(t-Butyldimethylsilyloxy)-cyclohex-2-en-1-one: A Formal Synthesis of (.+-.)-Mesembranol.