ArticleOrganic letters2007
Synthetic and biosynthetic studies on FR900482 and mitomycin C: an efficient and stereoselective hydroxymethylation of an advanced benzazocane intermediate.
Article in Organic letters, 2007. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 5 papers.
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Who cites it
5 citing papers in PubMed.
- Biosynthesis of DNA-Alkylating Antitumor Natural Products.Molecules (Basel, Switzerland) · 2022Review
- A gold(i)-catalysed approach towards harmalidine an elusive alkaloid fromRSC advances · 2022Article
- Synthetic Studies Towards the Mitomycins: Construction of the Tetracyclic Core via a Reductive Aminocyclization Reaction.Tetrahedron letters · 2009Article
- Mitomycins syntheses: a recent update.Beilstein journal of organic chemistry · 2009Article
- Synthesis of potential early-stage intermediates in the biosynthesis of FR900482 and mitomycin C.Organic letters · 2009Article
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Authors and funding
4 authors.
Funding
Abstract
We report a simple, efficient, and stereoselective Mukaiyama aldol approach to install the key hydroxymethyl moiety into the benzazocane framework of FR900482. Synthetic investigations revealed that the reaction is highly dependent upon the electronics of the aromatic ring. This approach enabled the economical introduction of a [13C] label to study the biosynthesis of these structurally and biogenetically related natural products. Epimerization of the initially formed beta-hydroxy ketone may enable access to mitomycin C or FR900482 biosynthetic congeners.
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