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Synthesis 2016; 48(24): 4555-4563
DOI: 10.1055/s-0036-1588079
DOI: 10.1055/s-0036-1588079
paper
Strategies towards the Synthesis of the Gilvocarcins
Further Information
Publication History
Received: 12 July 2016
Accepted after revision: 08 September 2016
Publication Date:
28 September 2016 (online)
Abstract
Two strategies for the synthesis of the gilvocarcins were explored in order to construct the C-arylglycosidic tricyclic core of these natural products. Whereas the addition of a complex naphthalene onto a carbohydrate-derived lactone, following Kishi’s protocol failed, the key C-glycosidic bond was successfully forged in a regio- and stereoselective manner through the use of TMS-acetylide as the nucleophile. Conversion of the alkyne into a diene and Diels–Alder cycloaddition with an in situ generated quinone allowed the assembling of a tricyclic structure which could serve as an advance synthetic intermediate for the synthesis of the gilvocarcins.
Supporting Information
- Supporting information for this article is available online at http://dx.doi.org/10.1055/s-0036-1588079.
- Supporting Information
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