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A McMurry Route to the Dienediyne Portion of Models of the Neocarzinostatin Chromophore
✍ Scribed by Elisabeth Rank; Reinhard Brückner
- Publisher
- John Wiley and Sons
- Year
- 1998
- Tongue
- English
- Weight
- 638 KB
- Volume
- 1998
- Category
- Article
- ISSN
- 1434-193X
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✦ Synopsis
The 6-ring/10-ring dienediyne model 11 of the antitumor agent neocarzinostatin chromophore 1 and its 6-ring/11-ring homolog 12 have been obtained in 41 and 18% yields, respectively, by McMurry cyclizations of ketoaldehydes 8 and 9 using TiCl 3 и2DME and Zn/Cu couple. Compounds 8 and 9 were obtained by multistep syntheses starting from the
📜 SIMILAR VOLUMES
The first 3--->6 type ring-closing dienediyne synthesis by means of a McMurry reaction was realized by converting the ketoaldehyde 20 into the 6-/10-membered bicyclic dienediyne 22. Diastereoselective pinacol couplings 20--->23 and 21--~24 giving 6-/10-membered bicyclic enediynediols were possible,
A 12-step synthesis of a dihydroxylated dienediyne analogue related to Neocarzinostatin Chromophore is