2005
DOI: 10.1021/ja042435i
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Abstract: Direct asymmetric aldol reactions constitute a powerful methodology for the efficient synthesis of complex natural products. Herein we report the first application of our recently reported dinuclear Zn-catalyzed direct aldol addition of alkynyl ketones to aldehydes in a short and efficient formal asymmetric synthesis of fostriecin, a potent cyctotoxic natural product. This work highlights not only the power of the aldol methodology but also the utility of the akynyl silane aldol adducts, as it is subsequently … Show more

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Cited by 129 publications
(44 citation statements)
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“…[xiii] TBS = tert -butyldimethylsilyl, TES = triethylsilyl, TPSH = 2,4,6-triisopropylbenzenesulfonyl hydrazide.…”
Section: Methodsmentioning
confidence: 99%
See 1 more Smart Citation
“…[xiii] TBS = tert -butyldimethylsilyl, TES = triethylsilyl, TPSH = 2,4,6-triisopropylbenzenesulfonyl hydrazide.…”
Section: Methodsmentioning
confidence: 99%
“…Such is the case in a formal synthesis of (+)-fostriecin (CI-920), in which an advanced intermediate, alkynylsilane 19 , bears a lactone and a hydroxyl group. [xiii] To obtain ( Z )-alkenylsilane 20 , diimide (generated in situ, using 2,4,6-triisopropylbenzenesulfonyl hydrazide (TPSH) and sodium bicarbonate) is used to reduce the triple bond in 19 . [xiv] A late stage TBAF-promoted alkenyl-alkenyl cross-coupling is subsequently carried out using 20 and alkenyl iodide 21 under mild conditions, with a concomitant deprotection, to afford target molecule 22 (Scheme 6).…”
Section: Sequential Cis-reduction/cross-couplingmentioning
confidence: 99%
“…136 Trost’s strategy takes advantage of a direct catalytic aldol catalyzed by a dinuclear zinc complex (ProPhenol) developed in his laboratories, 137 and a Hiayama cross-coupling reaction, also developed by Trost, 138 to unite the side chain to the core of fostriecin (Figure 12). The installation of the lactone was planned via an acylation/ring-closing metathesis, 91,92 a strategy that had been proven successful in previous syntheses.…”
Section: Fostriecinmentioning
confidence: 99%
“…In 2005, Trost and co-workers 33 described a formal synthesis of fostriecin (75) (Scheme 15). One of the steps of the synthesis consisted in the direct aldol reaction between ketone 85 and aldehyde 84, mediated by chiral binuclear zinc catalyst 83, which led to the formation of aldol adduct 86 with excellent level of enantioselectivity.…”
Section: Metal-catalyzed Direct Aldol Reactionsmentioning
confidence: 99%