A Concise Synthesis of the Pentacyclic Framework of Cortistatins

Yamashita, Shuji; Iso, Kentaro; Hirama, Masahiro

doi:10.1021/ol8012099

Cited by 84 publications

(25 citation statements)

References 22 publications

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“…4) 28,29 , which was obtained through the sequence of classical Mitsunobu reaction 31,32 , nickel-mediated reduction 33,34 , and modified Julia–Kocienski olefination (see Supporting Information for details) 35 . Compound 12 was then treated with 9-BBN to form an inseparable mixture of diastereoisomers in a ratio of 8:1 ( α / β ).…”

Section: Resultsmentioning

confidence: 99%

Total syntheses of shizukaols A and E

Tang

et al. 2018

Nat Commun

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Shizukaols possess a common heptacyclic framework containing more than ten contiguous stereocenters and potential biological activities. Here we report that the total syntheses of shizukaols A (1) and E (2), two lindenane-type dimers from the Chloranthaceae family, are achieved via a modified biomimetic Diels–Alder reaction. The common crucial biomimetic diene 23 and ethylene species (6, 17) are obtained through either a highly Z-selective olefination of α-siloxy ketone with ynolate anions or an intramolecular Horner–Wadsworth–Emmons olefination from commercially available Wieland–Miescher ketone (7). This synthetic approach here opens up practical avenues for the total syntheses of the intriguing Chloranthaceae family members, as well as the understanding of their relevant biological action in nature.

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Section: Resultsmentioning

confidence: 99%

Total syntheses of shizukaols A and E

Tang

et al. 2018

Nat Commun

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“…Recent routes have been attempted, with two being successful (see Scheme 11) [34][35][36]. In 2008, Hirama proposed using 1 to undergo a Knovengel condensation/electrocyclic reaction/radical cyclization strategy to afford cortistatin A-the most potent cortistatin [34]. Hydrindane 1 was transformed into 64 by NaBH4 reduction, protection of the alcohol with TBS-Cl, and alkylation.…”

Section: Hajos-parrish Dionementioning

confidence: 99%

Methodology for the Construction of the Bicyclo[4.3.0]nonane Core

Eddy

Ichalkaranje

2016

Molecules

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Abstract:The bicyclo[4.3.0]nonane scaffold, commonly known as a hydrindane, is a common structural motif found in many terpenoid structures and one that remains a challenge for synthetic chemists to elaborate with appropriate regio-and stereo-selectivity. Over the course of the study of terpene natural products, the elaboration of the hydrindane structure has seen progress on the utilization of both old and newer methods to achieve the desired outcomes. This review seeks to serve as a general overview of these methods, and detail specific examples.

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“…[11] Their collective efforts, commencing from a broad array of starting materials and guided by an assortment of creative strategies, have culminated in one semi-synthesis, [12] three total syntheses, [13][14][15] and two formal syntheses, [16] as well as a number of syntheses of the pentacyclic cortistatin core and some illuminating model studies. [17] In an attempt to present this synthetic work in a comprehensive yet palatable manner, these approaches are organized herein by the method for B ring formation.…”

Section: Synthetic Approaches To the Cortistatinsmentioning

confidence: 99%