Total Synthesis of Scytophycin C. 1. Stereoselective Syntheses of the C(1)−C(18) Segment and the C(19)−C(31) Segment

Nakamura, Ryoichi; Tanino, Keiji; Miyashita, Masaaki

doi:10.1021/ol035227o

Cited by 46 publications

(22 citation statements)

References 34 publications

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“…54), whose structure is close to swinholide A (181) stimulated the interest of various groups in its synthesis, that resulted in two very similar syntheses by Grieco and Speake 67 in 1997 and Miyashita et al 68 The two cytotoxic depsipeptides palau'amide (193) (Fig. 55) and aurilide (194) were synthesized by the groups of Yamada 9a and Ma, 69 respectively.…”

Section: Diastereoselective Processes Of Aldehyde-derived Dienolsmentioning

confidence: 99%

The vinylogous Mukaiyama aldol reaction (VMAR) in natural product synthesis

et al. 2014

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The vinylogous Mukaiyama aldol reaction (VMAR) allows efficient access to larger segments for complex natural product synthesis, primarily polyketides, through the construction of vicinal hydroxyl and methyl groups as well as di and tri-substituted double bonds in one single operation. In this review, we will highlight stereoselective protocols that have been used in natural product synthesis and cluster them into the four groups that can be obtained from different silyl ketene acetals or enol ethers. At the beginning, an overview on different stereoselective VMARs is presented; disregarding their applications in total syntheses.

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Section: Diastereoselective Processes Of Aldehyde-derived Dienolsmentioning

confidence: 99%

The vinylogous Mukaiyama aldol reaction (VMAR) in natural product synthesis

et al. 2014

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“…[150] Miyashita and co-workers recently reported the total synthesis of scytophcin C in which a crucial terminal amidation of a vinyl iodide was used at an advanced stage. [151] Under the Buchwald-modified Goldberg amidation conditions, the desired coupling product was formed in 85% yield.…”

Section: Addendummentioning

confidence: 99%

Modern Synthetic Methods for Copper‐Mediated C(aryl)O, C(aryl)N, and C(aryl)S Bond Formation

Ley,

Thomas

2003

Angew Chem Int Ed

2,517

816

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The copper-mediated C(aryl)[bond]N, C(aryl)[bond]O, and C(aryl)[bond]S bond formation is an important transformation and has been developed to include a wide range of substrates. This Review highlights the recent developments in the copper-mediated (both stoichiometric and catalytic) reactions of aryl boronic acids, aryl halides, iodonium salts, siloxanes, stannanes, plumbanes, bismuthates, and trifluoroborate salts as aryl donors. In particular, the recent introduction of boronic acids as reaction partners in both O- and N-arylation has been a significant discovery and will occupy centre-stage in this review. Clear improvements can be obtained by the correct choice of copper source, base, ligands, and other additives. Mechanistic investigations should provide insight into the catalytically active species, which would aid in the development of milder, more-efficient methods.

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“…Next, a Horner-Emmons olefination using aldehyde 10 and its subsequent acetylation gave the pentaacetate of preswinholide A (11) in 68% overall yield (from 9, Scheme 2.4) [12]. The potent biological properties of scytophycin C (17), its scarce availability from natural sources, and its close structural resemblance to the marine natural product swinholide A (8) have stimulated considerable interest in its synthesis and resulted in two very similar approaches performed by Grieco and Speake [13] and Miyashita [14] also using Paterson's VMAR protocol. Consequently, both groups obtained comparable yields and selectivities for the transformations on their proprietary segments 14 [13] and 16 [14] (Scheme 2.5, (1) and (2)).…”

Section: Aldehyde-derived Silyl Dienol Ethers -Diastereoselective Promentioning

confidence: 99%