Unified total synthesis of amorfrutins A and C via the Claisen rearrangement
نویسندگان
چکیده
منابع مشابه
Biomimetic total synthesis of forbesione and desoxymorellin utilizing a tandem Claisen/Diels--Alder/Claisen rearrangement.
A concise synthesis of forbesione (1) and desoxymorellin (3) is presented. Central to the strategy is a biomimetic Claisen/Diels-Alder/Claisen reaction cascade that proceeds in a regioselective manner and produces the desired scaffold exclusively. The observed regioselectivity and product distribution of the Claisen/Diels-Alder/Claisen reaction are attributed to the electronic effects of the xa...
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Reductive Claisen rearrangement of 1-allyloxy-8-methoxy-9, 10-anthraquinone followed by demethylation and reduction, and of 1,8-bisallyloxy-9,lO-anthraquinone followed by reduction provides regiospecific syntheses of 2-propyl- and 2,7-dipropyl anthralin
متن کاملUnified synthesis of caged Garcinia natural products based on a site-selective Claisen/Diels-Alder/Claisen rearrangement.
A unified synthetic strategy toward caged Garcinia natural products has been designed and implemented. Central to the strategy is a tandem Claisen/Diels-Alder/Claisen rearrangement of a suitably substituted xanthone precursor to form forbesione (1a). Serving as a template, forbesione is then used to deliver representative members of this family, including desoxygaudichaudione A (4), desoxymorel...
متن کاملPropargyl Claisen rearrangement: allene synthesis and beyond.
The propargyl Claisen rearrangement is a known protocol to gain access to functionalized allenes through the [3,3]-sigmatropic transformation of propargyl vinyl ethers. The correct use of appropriate propargyl vinyl ethers as starting materials coupled with suitable reaction conditions can aid in the development of new domino methodologies in which the allenes are valuable intermediates in rout...
متن کاملSynthesis of a simplified analogue of eleutherobin via a Claisen rearrangement and ring closing metathesis strategy.
The enantioselective synthesis of a simplified eleutherobin analogue by ring closing metathesis (RCM) of the 2,9-divinyl-substituted tetrahydro-oxonin is described; the analogue and an advanced intermediate revealed microtubule stabilising properties in the micromolar range.
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ژورنال
عنوان ژورنال: Bioscience, Biotechnology, and Biochemistry
سال: 2019
ISSN: 0916-8451,1347-6947
DOI: 10.1080/09168451.2019.1618699