Synthesis of (−)-alantrypinone

Hart, David J.; Magomedov, Nabi A.

doi:10.1016/s0040-4039(99)01005-9

Cited by 33 publications

(16 citation statements)

References 12 publications

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“…All these data suggested that compound 1 contains a pyrazino-[2,1-b]-quinazoline-3,6-dione moiety and an indole ring consistent with the results of X-ray diffraction analysis (Figure 3). We finally elucidated the structure of compound 1 as (-)-(1R,4R)-1,4-(2,3)-indolmethane-1-methyl-2,4-dihydro-1H-pyrazino-[2,1-b]-quinazoline-3,6-dione, a known quinazoline alkaloid synthesized as a precursor for (-)-alantrypinone (Hart & Magomedov, 1999). To the best of our knowledge, this is the first time that compound 1 has been found in plant endophytes, although fungi belonging to the genera Penicillium serve as a rich source of alkaloids clearly derived from amino acids (Hart & Magomedov, 2001).…”

mentioning

confidence: 99%

Identification of a quinazoline alkaloid produced byPenicillium vinaceum, an endophytic fungus fromCrocus sativus

Zheng¹,

Li²,

Zou³

et al. 2011

Pharmaceutical Biology

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mentioning

confidence: 99%

Identification of a quinazoline alkaloid produced byPenicillium vinaceum, an endophytic fungus fromCrocus sativus

Zheng¹,

Li²,

Zou³

et al. 2011

Pharmaceutical Biology

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“…22,23 This research was actually a diversion of a synthetic program directed at spiroquinazoline 1, whose synthesis from Ltryptophan was being pursued when the structure of 7 was reported. 6 The late stages of the synthetic plan were inspired by the biosynthetic speculation described in Section 3 of this review (Scheme 1).…”

Section: Total Synthesis Of Alantrypinone (7) and Ent-alantrypinone (mentioning

confidence: 99%

“…An approach to spiroquinazoline that is very different from either the cycloaddition or Nacyliminium ion routes has recently been described (Schemes [20][21][22]. 46 The plan (Scheme 20)…”

Section: Scheme 14mentioning

confidence: 99%

The spiroquinazoline family of alkaloids: a review

Hart¹

2010

Arkivoc

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“…However, both Snider [49] and Hart [50] have repeated the Ganesan fumiquinazoline G synthesis and have revised the assignment of structure 42. However, both Snider [49] and Hart [50] have repeated the Ganesan fumiquinazoline G synthesis and have revised the assignment of structure 42.…”

Section: 132-anthranilic Acid As the Second Residuementioning

confidence: 99%

Chemistry of Pyrazino[2,1-b]quinazoline-3,6-diones

Avendaño¹,

Menéndez

2003

COC

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The pyrazino[2,1-b]quinazoline-3,6-dione system is the key structural fragment of a group of alkaloids. The synthesis of derivatives of this system has been accomplished by means of three kinds of methods, starting from 4(3H)-quinazolinones, 2,5-piperazinediones or open-chain tripeptides, where anthranilic acid can be at the C-terminal, the N-terminal or the intermediate position of the tripeptide. Regarding its reactivity, much work has been developed to show that the system behaves as a glycine template. Thus, its C-1 position can be deprotonated by strong bases, and the anion thus generated undergoes stereoselective alkylations, acylations and Michael reactions. Hypervalent iodine reagents commonly employed for the α-functionalization of ketones also react at C-1, leading to electrophilic species that can be arylated and therefore used as precursors to polycyclic derivatives. Oxidation and Mannich reactions also occur at the C-1 position and lead to precursors of tertiary iminium cations. Some rearrangement reactions have been described, including a pyrazine-pyridine transformation and a transannular rearrangement that has ben proposed to explain some reactivity results. The aromatic ring of pyrazino[2,1-b]quinazoline-3,6-diones can be easily hydrogenated to give tetrahydro derivatives.

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Synthesis of (−)-alantrypinone

Cited by 33 publications

References 12 publications

Identification of a quinazoline alkaloid produced byPenicillium vinaceum, an endophytic fungus fromCrocus sativus

Identification of a quinazoline alkaloid produced byPenicillium vinaceum, an endophytic fungus fromCrocus sativus

The spiroquinazoline family of alkaloids: a review

Chemistry of Pyrazino[2,1-b]quinazoline-3,6-diones

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