A Tandem Prins/Schmidt Reaction Approach to Marine Alkaloids: Formal and Total Syntheses of Lepadiformines A and C

Meyer, Angelica M.; Katz, C. E.; Li, Sze Wan; Velde, David Vander; Aubé, Jeffrey

doi:10.1021/ol100113r

Cited by 65 publications

(22 citation statements)

References 30 publications

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“…To use the Diels–Alder/Schmidt chemistry in panels a and d , we needed to explore new variations using highly substituted dienes. Schmidt reactions related to those shown in panels b and c were first developed during total synthesis efforts toward lepadiformine and cylindricine alkaloids 39 , 40 . The azido alcohol-mediated Schmidt reaction has been previously used for building a library of γ-turn mimetics 41 .…”

Section: Resultsmentioning

confidence: 99%

Probing chemical space with alkaloid-inspired libraries

et al. 2014

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Screening of small molecule libraries is an important aspect of probe and drug discovery science. Numerous authors have suggested that bioactive natural products are attractive starting points for such libraries, due to their structural complexity and sp3-rich character. Here, we describe the construction of a screening library based on representative members of four families of biologically active alkaloids (Stemonaceae, the structurally related cyclindricine and lepadiformine families, lupin, and Amaryllidaceae). In each case, scaffolds were based on structures of the naturally occurring compounds or a close derivative. Scaffold preparation was pursued following the development of appropriate enabling chemical methods. Diversification provided 686 new compounds suitable for screening. The libraries thus prepared had structural characteristics, including sp3 content, comparable to a basis set of representative natural products and were highly rule-of-five compliant.

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Section: Resultsmentioning

confidence: 99%

Probing chemical space with alkaloid-inspired libraries

et al. 2014

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“…Aubé and co-workers reported the formal and total synthesis of (±)-lepadiformine A [(±)-14] and (±)-lepadiformine C [(±)-16] by using a sequence of the Prins and Schmidt reactions (Scheme 18). 54 Treatment of cyclopropane 120 and azidoaldehydes 121a,b in the presence of Scheme 17 Formal synthesis of (±)-lepadiformine C by Renaud and coworkers…”

Section: From B Ringmentioning

confidence: 99%

Synthesis of Tricyclic Marine Alkaloids, Cylindricines, Lepadiformines, Fasicularin, and Polycitorols: A Recent Update

Kaga

Chiba

2017

Synthesis

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Cylindricines, lepadiformines, and fasicularin are tricyclic marine alkaloids bearing perhydropyrrolo- and pyrido[2,1-j] frameworks having divergent chemical functionalities. They have been isolated from marine tunicates over the last two decades and found to have a range of cytotoxicity such as DNA-alkylating ability. Recently, polycitorols have emerged as a new member of this alkaloid family. Their unique structural features and biological activities have intrigued many researchers and challenged them in their synthesis. This review describes recent syntheses of the tricyclic alkaloids based on key synthetic approaches.1 Introduction2 Total and Formal Syntheses2.1 Overview of Synthetic Strategies2.2 Azaspirocycle (BC Ring) Approaches2.3 Indolizidine (AC Ring) Approaches2.4 Azadecalin (AB Ring) Approaches2.5 Tandem Cyclization Approaches3 Summary and Future Perspective

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“…Formal synthesis of lepadiformine C Lepadiformine C was recently isolated from Clavelina moluccensis [47] and since then, two syntheses of the alkaloid have been accomplished [48,49]. In Aubé's synthesis [48], a lactam intermediate closely related to the one of our lepadiformine A intermediate [16] was prepared.…”

Section: Synthesis Of Monomorine Imentioning

confidence: 99%

“…In Aubé's synthesis [48], a lactam intermediate closely related to the one of our lepadiformine A intermediate [16] was prepared. As an illustration of the synthetic usefulness of the desulfitative carboazidation, we achieved a concise synthesis of Aubé's intermediate (Scheme 12) [22].…”

Section: Synthesis Of Monomorine Imentioning

confidence: 99%

Radical azidation reactions and their application in the synthesis of alkaloids

Lapointe

Kapat

Weidner

et al. 2012

Pure and Applied Chemistry

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Recent advances in radical azidation using sulfonyl azides are presented. For instance, radical carboazidation using α-iodoketones, desulfitative carboazidation, and antiMarkovnikov hydroazidation of alkenes are described. These novel methods tolerate a large number of functional groups and allow the synthesis of organic azides that would be difficult to synthesize otherwise. The transformation of the azides using reductive processes as well as a Schmidt reaction under nonacidic conditions were used to synthesize alkaloids including indolizidine 167B, monomorine I, cylindricine C, and lepadiformine C.

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A Tandem Prins/Schmidt Reaction Approach to Marine Alkaloids: Formal and Total Syntheses of Lepadiformines A and C

Cited by 65 publications

References 30 publications

Probing chemical space with alkaloid-inspired libraries

Probing chemical space with alkaloid-inspired libraries

Synthesis of Tricyclic Marine Alkaloids, Cylindricines, Lepadiformines, Fasicularin, and Polycitorols: A Recent Update

Radical azidation reactions and their application in the synthesis of alkaloids

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