Stereocontrolled synthesis of lepadiformine A

Lygo, Barry; Kirton, Eirene H. M.; Lumley, Christopher

doi:10.1039/b805951a

Cited by 26 publications

(6 citation statements)

References 55 publications

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“…These structurally related compounds all exhibited bioactivity against brine shrimp larvae in a bioassay. The tricyclic ring system of cylindricine C is closely related to the one found in lepadiformine A, , differing only in the cis / trans junction of the perhydroquinoline ring and the ketone at C(4).…”

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confidence: 87%

Total Synthesis of (±)-Cylindricine C

2011

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A concise synthesis of (±)-cylindricine C and its C(13)-epimer is described. Starting from 1-octyne, cylindricine C and 13-epi-cylindricine C were prepared in 11% and 15% yields, respectively. The synthesis involves the preparation of the central tricyclic moiety via a radical α-iodoketone carboazidation/bis-reductive amination sequence. Inversion of the stereochemistry at C(13) and C(5) was efficiently achieved on late stage intermediates.

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confidence: 87%

Total Synthesis of (±)-Cylindricine C

2011

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“…Lygo and co-workers reported the synthesis of (±)-lepadiformine A [(±)-14] using the intramolecular hetero-Diels-Alder cycloaddition as a key step (Scheme 21). 59,60 The reaction of C-ring cyclic imine ester 141 having a 1,3diene moiety in 1,1,1,3,3-hexafluoropropan-2-ol (HFIP) allowed the cleavage of the tert-butyl ester to generate iminium-carboxylate zwitterion 142. Subsequent intramolecular cycloaddition reaction of 142 via an endo transition state provided tricycle 143 as the major isomer (dr = 5:1).…”

Section: From C 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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“…57 This tricyclic alkaloid has been isolated from several species of Clavenia and Polycitoridae sea squirts and is moderately cytotoxic toward various tumor cell lines and effective to block potassium ion channels. Initial attempts to perform the aza DielsAlder reaction with the racemic imino-diene t-butyl ester 134 in toluene at temperatures up to 165 C did not lead to the observation of any cycloadducts but to double bonds isomerization products.…”

Section: Aziridinesmentioning

confidence: 99%

Cycloadditions with StereoselectiveCNBond Formation in Total Syntheses

Vincent

2013

Stereoselective Synthesis of Drugs and Natural Products

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Cycloadditions reactions are very efficient tools for the constructions of multiple bonds in one step and are therefore methods of choice for the total synthesis of natural products and drugs. The use of a terminal nitrogen containing partner allows for the stereoselective formations of a CN bond. Because of the vast number of nitrogen containing compounds available, this field has found a widespread interest in total synthesis. This chapter will cover the cycloadditions in which a CN bond is formed. It will be devoted to the description of [2+2], [3+2], [3+3], [4+2], and [2+2+2] processes that are key steps in total synthesis with imine, nitroso, azo, isocyanate, azomethine imine, azide, or azadiene reagents. A discussion of regioselectivity, diastereoselectivity, and enantioselectivity issues will be provided for each reaction.

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Stereocontrolled synthesis of lepadiformine A

Cited by 26 publications

References 55 publications

Total Synthesis of (±)-Cylindricine C

Total Synthesis of (±)-Cylindricine C

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

Cycloadditions with StereoselectiveCNBond Formation in Total Syntheses

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