Synthesis of 12-Methyl-1, 2, 3, 4, 6, 7, 12, 12b-octahydro-2, 6-methanoindolo[2, 3-a]quinokizine
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12-Methyl-1, 2, 3, 4, 6, 7, 12, 12b-octahydro-2, 6-methanoindolo [2, 3-a] quinolizine (I), which represents the fundamental skeleton of sarpagine type indole alkaloids, was synthesized. Thus methyl ester (XI) hydrochloride of N-benzyl-1-methyltryptophan was treated with methy 3-formylpropionate to form tetrahydro-β-carboline derivative (XV), from which 6, 10-imino-5H-cyclooct [b] indole dervative (XVII) was prepared by Dieckmann cyclization with sodium hydride under a certain working condition. This was condensed with methyl bromoacetate followed by ketone fission to yield ketoester (XX), from which N-benzyl group was reductively removed and then converted to N-methyl derivative (XXIII).The ethylene thioketal (XXV) of the latter was desulfurized as usual and the product was reduced by lithium aluminum hydride to furnish the corresponding alcohol (XXVII), which was tosylated with tosyl chloride in pyridine in the cold. Spontaneous quaternization of the tosylate took place forming the cyclized quaternary base (XXVIII), the chloride salt of which was submitted to pyrolysis reaction to produced the desired base (I).
収録刊行物
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- CHEMICAL & PHARMACEUTICAL BULLETIN
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CHEMICAL & PHARMACEUTICAL BULLETIN 13 (10), 1231-1240, 1965
公益社団法人 日本薬学会
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詳細情報
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- CRID
- 1390001204174021760
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- NII論文ID
- 110003619480
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- NII書誌ID
- AA00602100
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- ISSN
- 13475223
- 00092363
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- PubMed
- 5864705
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- 本文言語コード
- en
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- データソース種別
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- JaLC
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- PubMed
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- 使用不可