The pioneering work of Wong et al in 1971-73' was the first of a growing series of investigations toward the efficient laboratory synthesis of clinically useful anthracycline antibiotics. Although several total syntheses of (\*)-daunomycinone (IIIa) and adriamycinone (IIIb) have been reported,' only
A regiospecific total synthesis of ellipticine via nitrene insertion
β Scribed by R.Bryan Miller; Sundeep Dugar
- Publisher
- Elsevier Science
- Year
- 1989
- Tongue
- French
- Weight
- 183 KB
- Volume
- 30
- Category
- Article
- ISSN
- 0040-4039
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β¦ Synopsis
Ellipticine, a 6H-pyrido[4,3_b]carbazole alkaloid, has been regiospecifically synthesized by a general route which should allow for the preparation of a number of derivatives. The approach employs a versatile coupling reaction between phenylboronic acid and a substituted bromoisoquinoline followed by carbazole ring formation via a nitrene insertion reaction to give ellipticine.
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This communication describes a solution to the general problem of the regiospecific synthesis of an unsymmetrically substituted anthraquinone system. Acetogenins containing this moiety are frequently encountered as antibiotics,' and the system is characteristic of the clinically important anthracycl