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Total Syntheses of Tanshinone-I, Tanshinone-II and Cryptotanshinone

Yoshinobu Inouye, +1 more
- 01 Nov 1969 - 
- Vol. 42, Iss: 11, pp 3318-3323
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TLDR
In this article, the effect of substituents for orientation phenomena can be considered to be of electronic nature, and preliminary accounts for the Diels-Alder reaction of methoxybenzoquinone revealed that the effect on orientation properties can be assumed to be electronic.
Abstract
Total syntheses of tanshinone-II (II) and cryptotanshinone (III) from 3-methylbenzofuran-4, 7-quinone (X) and 6,6-dimethyl-l-vinylcyclohexene (IX), and of tanshinone-I (I) from quinone X and o-methylstyrene (XVIII) are described. Preliminary accounts for the Diels-Alder reaction of methoxybenzoquinone revealed that the effect of substituents for orientation phenomena can be considered to be of electronic nature.

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Citations
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Biosynthesis, total syntheses, and antitumor activity of tanshinones and their analogs as potential therapeutic agents

TL;DR: The biosynthesis, total syntheses, and antitumor activities of tanshinones,especially neo-tanshinlactone and its analogs are discussed.

Natural products possessing protein tyrosine phosphatase 1B (PTP1B) inhibitory activity found in the last decades

TL;DR: This article provides an overview of approximately 300 secondary metabolites with inhibitory activity against protein tyrosine phosphatase 1B (PTP1B), which were isolated from various natural sources or derived from synthetic process in the last decades.
Journal ArticleDOI

Total synthesis of dan shen diterpenoid quinones

TL;DR: A photochemical aromatic annulation strategy provides efficient synthetic routes to the diterpenoid quinones (+)-danshexinkun A, danshex-inkun B, Danshexin-C, (−)-dihydrotanshinone I, and tansinone I.
Journal ArticleDOI

Synthesis and biological evaluation of (±)-cryptotanshinone and its simplified analogues as potent CDC25 inhibitors

TL;DR: Cryptotanshinone and its simplified analogues were synthesized via SmI2 promoted radical cyclization to construct the furan ring and were identified as effective inhibitors of dual specificity protein phosphatase CDC25B and inhibited growth in A-549 human lung cancer cell line.
Journal ArticleDOI

Total Synthesis of Neo‐Tanshinlactones through a Cascade Benzannulation‐Lactonization as the Key Step

TL;DR: In this article, a cascade annulation-lactonization of phthalides with α-carboxyfurylacrylates in the presence of lithium hexamethyldisilazide (LiHMDS) provides both convergent and semiconvergent regioselective syntheses of neo-tanshinlactones in moderate yields.
References
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Journal ArticleDOI

Diels‐Alder reactions II: The Reaction Mechanism

TL;DR: The possible mechanisms of the preparatively so productive Diels-Alder reactions are discussed critically on the basis of experimental data as discussed by the authors, although most of the facts can be explained readily by a synchronous mechanism, a number of problems remains.
Journal ArticleDOI

Reaktionen mit Nitrosodisulfonat, V. Mitteil.): Über die Bildung von Naphtochinonen†

TL;DR: In this paper, ausnahmsweise werden hier p- und o-Chinon nebeneinander gebildet 26-Dioxy-naphthalin wird nicht zu amphi-Naphthochinon dehydriert, sondern zu 6-Oxynaphthocinon-(12) oxydiert 2-Oxy-anthracen verhalt sich wie Naphthol-(2); 8-OXY-chinolin geht in Chinolinch
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