Enantioselective synthesis of the quinolizidine alkaloids (+)-myrtine and (−)-epimyrtine

Gardette, D.; Gelas-Mialhe, Yvonne; Gramain, Jean-Claude; Perrin, Bertrand; Remuson, Roland

doi:10.1016/s0957-4166(98)00170-0

Cited by 35 publications

(26 citation statements)

References 20 publications

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“…Since it has been isolated, numerous total syntheses of this alkaloid in racemic form have been reported in the literature. However, only a few asymmetric syntheses of (−)-epimyrtine have been described to date including the intramolecular allylsilane N -acyliminium ion cyclization [6], the organocatalytic aza-Michael reaction [7], the intramolecular Mannich reaction [8], and the iminium ion cascade reaction [9–10]. More efficient, convenient and highly stereoselective synthetic routes are still being sought after.…”

Section: Resultsmentioning

confidence: 99%

Total synthesis of (−)-epimyrtine by a gold-catalyzed hydroamination approach

Trinh¹,

Nguyen²,

Amaral³

et al. 2013

Beilstein J. Org. Chem.

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Section: Resultsmentioning

confidence: 99%

Total synthesis of (−)-epimyrtine by a gold-catalyzed hydroamination approach

Trinh¹,

Nguyen²,

Amaral³

et al. 2013

Beilstein J. Org. Chem.

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“…28 Condensation of known 29 Back and co-workers also reported the synthesis of myrtine (2.4) using a similar strategy to their lasubine II synthesis (Scheme 9). 33 Conjugate addition of racemic amine 8.3 to alkyne 9.1 followed by cyclization generated enone 9.2 in 42% yields over two steps.…”

Section: Scheme 4 Pilli's Synthesis Of Myrtine and Lasubine IImentioning

confidence: 99%

Synthesis of quinolizidine-containing lycopodium alkaloids and related natural products

Veerasamy

Carter

2016

Tetrahedron

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“…This synthesis constitutes the first total synthesis of naturally occurring (-)-epimyrtine and confirms the configuration 4 R ,10 S which was assigned previously to this compound. [ 53 ]…”

Section: Quinolizidinesmentioning

confidence: 99%

A convenient allylsilane-N-acyliminium route toward indolizidine and quinolizidine alkaloids

Remuson¹

2007

Beilstein J. Org. Chem.

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This review relates all the results that we obtained in the field of the total synthesis of indolizidine and quinolizidine alkaloids using a strategy of the addition of an allylsilane on an N-acyliminium ion. In this paper, we describe the synthesis of racemic indolizidine 167B and chiral indolizidines: (-)-indolizidines 167B, 195B, 223AB, (+)-monomorine, (-)-(3R,5S,8aS)-3-butyl-5-propylindolizidine and (-)-dendroprimine. Next, we relate the synthesis that we have developed in the quinolizidines field: (±)-myrtine and epimyrtine, (±)-lasubines I and II and chiral quinolizidines: (+)-myrtine, (-)-epimyrtine, (-)-lasubines I and II and (+)-subcosine II.

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Enantioselective synthesis of the quinolizidine alkaloids (+)-myrtine and (−)-epimyrtine

Cited by 35 publications

References 20 publications

Total synthesis of (−)-epimyrtine by a gold-catalyzed hydroamination approach

Total synthesis of (−)-epimyrtine by a gold-catalyzed hydroamination approach

Synthesis of quinolizidine-containing lycopodium alkaloids and related natural products

A convenient allylsilane-N-acyliminium route toward indolizidine and quinolizidine alkaloids

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