Calyciphylline B-type Alkaloids: Evolution of a Synthetic Strategy to (-)-Daphlongamine H.

We provide a full account of our synthetic studies targeting the hexacyclic calyciphylline B-type alkaloids, a subfamily of the Daphniphyllum natural products. Following an initial set of synthetic strategies focused on constructing the piperidine core of the calyciphylline B-type framework via a 6π-azaelectrocyclization, as well as exploiting the reactivity of underexplored oxazaborinine heterocycles, we ultimately designed a highly functionalized acyclic precursor which underwent carefully orchestrated and efficient cyclizations to forge the architecturally complex natural product scaffold. Our efforts have culminated in the development of the first total synthesis of (-)-daphlongamine H, provided access to its C5-epimer, (-)-isodaphlongamine H, and led to structural revision of deoxyisocalyciphylline B

The First Total Synthesis of Dragmacidin D

The first total synthesis of the biologically significant bis-indole alkaloid dragmacidin D (5) has been achieved. Thermal and electronic modulation provides the key for a series of palladium-catalyzed Suzuki cross-coupling reactions that furnished the core structure of the complex guanidine- and aminoimidazole-containing dragmacidins. Following this crucial sequence, a succession of meticulously controlled final events was developed leading to the completion of the natural product

Organic Chemistry: A Call to Action for Diversity and Inclusion

By now, most of us in the field of organic chemistry have become aware of the recent Perspective Article by Hudlicky published on the Angewandte Chemie, International Edition website(1) and then quickly removed as a result of rapid and strong denunciation on social media and in other forums. We have had complex emotional responses to the opinions expressed in this piece regarding the effects of diversity and inclusion efforts in chemistry: anger, that such regressive views were provided a platform in one of our leading chemistry journals; surprise, that the piece made it through the peer review process; and disappointment, that these views continue to persist, despite our hope that the climate for researchers in organic chemistry had improved since we were all trainees

Organic Chemistry: A Call to Action for Diversity and Inclusion

By now, most of us in the field of organic chemistry have become aware of the recent Perspective Article by Hudlicky published on the Angewandte Chemie, International Edition website(1) and then quickly removed as a result of rapid and strong denunciation on social media and in other forums. We have had complex emotional responses to the opinions expressed in this piece regarding the effects of diversity and inclusion efforts in chemistry: anger, that such regressive views were provided a platform in one of our leading chemistry journals; surprise, that the piece made it through the peer review process; and disappointment, that these views continue to persist, despite our hope that the climate for researchers in organic chemistry had improved since we were all trainees

Organic Chemistry: A Call to Action for Diversity and Inclusion

By now, most of us in the field of organic chemistry have become aware of the recent Perspective Article by Hudlicky published on the Angewandte Chemie, International Edition website(1) and then quickly removed as a result of rapid and strong denunciation on social media and in other forums. We have had complex emotional responses to the opinions expressed in this piece regarding the effects of diversity and inclusion efforts in chemistry: anger, that such regressive views were provided a platform in one of our leading chemistry journals; surprise, that the piece made it through the peer review process; and disappointment, that these views continue to persist, despite our hope that the climate for researchers in organic chemistry had improved since we were all trainees

Toward a Symphony of Reactivity: Cascades Involving Catalysis and Sigmatropic Rearrangements

Catalysis and synthesis are intimately linked in modern organic chemistry. The synthesis of complex molecules is an ever evolving area of science. In many regards, the inherent beauty associated with a synthetic sequence can be linked to a certain combination of the creativity with which a sequence is designed and the overall efficiency with which the ultimate process is performed. In synthesis, as in other endeavors, beauty is very much in the eyes of the beholder.† It is with this in mind that we will attempt to review an area of synthesis that has fascinated us and that we find extraordinarily beautiful, namely the combination of catalysis and sigmatropic rearrangements in consecutive and cascade sequences