Selective Prenylation of Protected Phenols for Synthesis of Pawhuskin A Analogues

Gardner, Kevyn D.; Wiemer, David F.

doi:10.1021/acs.joc.5b02756

Cited by 7 publications

(20 citation statements)

References 44 publications

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“…By treatment of bromide 54 under similar halogen metal exchange conditions, but in THF instead of Et 2 O, the ratio of the two products approximately reversed and the alkylated compound 55 was the major product. 42 A similar and equally dramatic solvent effect has been reported by Bridges and coworkers. 51 NaH, CH 3 Figure 16.…”

Section: Chapter 2 Selective Synthesis Of A-ring Isomers For Analoguesupporting

confidence: 74%

“…By changing the base from NaH to LiHMDS, it was clear by 31 P NMR that the major product again was alkylation at the carbon alpha to the phosphonate. 42 Although prenylation at the alpha carbon originally was not desired, when it became important a more efficient synthetic route towards this prenyl compound was developed. This approach could be based upon treatment of phosphonate 35 with only one equivalent of LiHMDS and it was found that these more simplistic conditions could provide the prenyl compound 36 in great yield.…”

Section: Chapter 2 Selective Synthesis Of A-ring Isomers For Analoguementioning

confidence: 99%

“…Deprotection of the silyl group in all three isomers under standard TBAF conditions was achieved in good yield. 42 26 Figure 18. Halogen metal exchange sequence with TBS ethers 58-60…”

Section: Chapter 2 Selective Synthesis Of A-ring Isomers For Analoguementioning

confidence: 99%

“…Purification of the desired alcohols via column chromatography verified the anticipated low yields based on the TLC analyses, and compound 26 was obtained in a disappointing yield as a mixture with a MOM deprotected side product. 42 1) n-BuLi, THF -78 °C Figure 19. Halogen metal exchange sequence with THP ethers 64-66 (*isolated as mixture)…”

Section: Chapter 2 Selective Synthesis Of A-ring Isomers For Analoguementioning

confidence: 99%

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Synthesis of potential opioids based on the natural Pawhuskins

Gardner¹

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Nothing in life is to be feared, it is only to be understood. Now is the time to understand more, so that we may fear less. Marie Curie iii ACKNOWLEDGEMENTS To begin with, this thesis would not be here today if were not for the inspiration, given to me by my professors at Cal Poly Pomona, to continue my education with graduate school. I am incredibly grateful to have had Dr. David Wiemer as an advisor at the University of Iowa, as I value the considerable amount of knowledge and wisdom that he has bestowed on me during my time in graduate school. I cannot thank him enough for his continuous kindness, encouragement, and his extraordinary level of patience, it is truly admirable. Life in the lab would not have been the same without my fellow lab mates past and present. Thank you to Dr. John Kodet and all the other past students who continued to be of assistance beyond their time in the group. Particular thanks should go to Dr. Alyssa Hartung for her guidance when I started my work in the lab and providing several samples for my pawhuskin research, as well as Dr. Jeffrey Neighbors for testing my compounds and his continued collaboration. I would like to thank Carrie Meyers for her assistance in the lab as an undergraduate researcher. For Dr. Veronica Wills, Dr. Rebekah Shippy, and the current students, I am appreciative of all of your support through the new friendships I have formed and for always being there to help solve problems in the lab. The faculty and staff of the Department of Chemistry have been profoundly helpful and supportive throughout my time here in Iowa. I am very grateful for all that they do and for my fellow students in the department who have helped make my graduate iv school experience that much more enjoyable. I would also like to thank the Roy J. Carver Trust for the financial support that allowed me to spend more time in the lab. This journey would have been more trying if it were not for the relentless support and continued encouragement from my parents and the rest of my family. It was always reassuring to know that they were constantly right behind me, cheering me on. Last, but certainly not least, I want to thank my wonderful husband for his constant encouragement and support. Throughout my years in graduate school, he has always been understanding of all the time I have spent in the lab and on my computer at home; and often found ways to help me dedicate even more time towards research. He is incredibly patient, especially when I talk endlessly about chemistry. I have always enjoyed his take on what I do; even when he constantly reminds me that a geranyl chain resembles a staircase. Thank you, Joe, for being one of my biggest supporters, and always finding ways to bring laughter into every single one of my days.

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Section: Chapter 2 Selective Synthesis Of A-ring Isomers For Analoguesupporting

confidence: 74%

Section: Chapter 2 Selective Synthesis Of A-ring Isomers For Analoguementioning

confidence: 99%

“…Deprotection of the silyl group in all three isomers under standard TBAF conditions was achieved in good yield. 42 26 Figure 18. Halogen metal exchange sequence with TBS ethers 58-60…”

Section: Chapter 2 Selective Synthesis Of A-ring Isomers For Analoguementioning

confidence: 99%

Section: Chapter 2 Selective Synthesis Of A-ring Isomers For Analoguementioning

confidence: 99%

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Synthesis of potential opioids based on the natural Pawhuskins

Gardner¹

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“…The MOM ester 19 proved to be sufficiently stable to allow halogen-metal exchange and alkylation with geranyl bromide to give the ester 20 in moderate yield. 24 …”

Section: Resultsmentioning

confidence: 99%

Synthesis of amide isosteres of schweinfurthin-based stilbenes

Stockdale

Beutler

Wiemer

2017

Bioorganic & Medicinal Chemistry

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The schweinfurthins are plant-derived stilbenes with an intriguing profile of anti-cancer activity. To obtain analogues of the schweinfurthins that might preserve the biological activity but have greater water solubility, a formal replacement of the central olefin with an amide has been explored. Two pairs of amides have been prepared, each containing the same hexahydroxanthene “left half” joined through an amide linkage to two different “right halves.” In each series, the amide has been inserted in both possible orientations, placing the carbonyl group on the tricyclic ABC ring system and the amine on the D-ring, or placing the amine on the hexahydroxanthene and the carbonyl group on the D-ring. The four new schweinfurthin analogues have been tested in the NCI 60 cell line screen, and in both cases the more active isomer carried the carbonyl group on the C-ring.

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