Journal ArticleDOI
Synthetic routes to (±)-daunomycinone: elaboration of the hydroxy-ketone group from an α-tetralone derivative, and selective methylation of the C(4)-hydroxy group using diazomethane
Robert J. Blade,Philip Hodge +1 more
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In this paper, a 12-step synthetic route to (±)-daunomycinone was described, which uses Friedel-Crafts reactions to assemble the ring system; (−)-carminomycinones reacts with diazomethane to give (+)-Daunomycinone.Abstract:
A 12-step synthetic route to (±)-daunomycinone is described which uses Friedel–Crafts reactions to assemble the ring system; (–)-carminomycinone reacts with diazomethane to give (+)-daunomycinone.read more
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Book ChapterDOI
Chapter 28 Synthetic Approaches to Anthracycline Antibiotics
TL;DR: In this article, the synthesis of the anthracyclines is divided into three parts: construction of the aglycones synthesis of sugar residue and coupling of the two.
Book ChapterDOI
Recent studies on doxorubicin and its analogues.
Jeffrey R. Brown,S. Haider Imam +1 more
TL;DR: This chapter focuses on synthetic routes to doxorubicin and other anthracyclines and discusses the biochemical effects of dox orubic in and analogues of doXorubICin.
Journal ArticleDOI
A doubly-convergent and regioselective synthesis of (±)-daunomycinone
Joaquin Tamariz,Pierre Vogel +1 more
TL;DR: The monoadduct of benzoquinone to 2,3,5,6-tetramethylidene-7-oxabicyclo[2.2. l]heptane (7) was transformed into (1RS,4RS, 4aSR)-2,3-dimethylidenes-l,4-epoxy-l 2, 3,4,4a,10-hexahydro-8-methoxyanthracene (28) as discussed by the authors.
Journal ArticleDOI
Selective 19F-Labeling of Functionalized Carboxylic Acids with Difluoromethyl Diazomethane (CF2HCHN2)
TL;DR: The recently developed reagent-CF2 HCHN2 -selectively esterifies carboxyl groups on organic molecules in the presence of other polar functional groups, allowing "last-step" incorporation of a fluorinated ester moiety into organic structures, including bioorganic molecules such as peptides and proteins.
Journal ArticleDOI
Regioselektive synthese von daunomycinon und γ-rhodomycinon
TL;DR: In this paper, the Grignard reagents 9b and 9d were added to the anhydride to synthesize daunomycinone and γ-rhodomecinone.