Total Synthesis of Swinholide A, Preswinholide A, and Hemiswinholide A

Nicolaou, K. C.; Patron, A. P.; Ajito, Katsuhiro; Richter, P; Khatuya, Haripada; Bertinato, Peter; Miller, Ross A.; Tomaszewski, M. J.

doi:10.1002/chem.19960020718

Cited by 112 publications

(56 citation statements)

References 82 publications

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“…The synthesis began with commercially available cis-butenediol (7), which was selectively protected with freshly prepared 4-methoxybenzyl-2,2,2-trichloroacetimidate and a catalytic amount of (-)-camphor-10-sulfonic acid (CSA) in dichloromethane to give mono-PMB ether 8 [5] (Scheme 2). Resulting allyl alcohol 8 was converted into its allyl bromide by using Appel reaction conditions [6,7] to afford compound 6 in 94 % yield, which was further treated with 1-heptyne by using a Cu I -mediated cross-coupling reaction [7] to give 9 in 96 % yield.…”

Section: Resultsmentioning

confidence: 99%

The First Total Synthesis of Topsentolide B₃

et al. 2011

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Section: Resultsmentioning

confidence: 99%

The First Total Synthesis of Topsentolide B₃

et al. 2011

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“…Silylation of 30 gave ether 31 which was smoothly converted into Weinreb amide 29 by oxidative alkene cleavage, Wittig extension and hydrogenation.Coupling fragment 28 was synthesized from known alcohol 32 30 by protection, alkene cleavage and Corey-Fuchs 31 alkyne formation. Treatment of the alkyne 32 with n-BuLi followed by addition of the amide 29 and subsequent complete saturation using H 2 and Lindlar catalyst gave the corresponding ketone 33 in excellent yield without any benzyl group removal.…”

Section: Methodsmentioning

confidence: 99%

Total synthesis of spiroketal containing natural products: kinetic vs. thermodynamic approaches

Sous¹,

Ganame²,

Zanatta³

et al. 2006

Arkivoc

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This review details part of a lecture delivered at the 20 th ICHC in Palermo Italy, July 31-August 5 2005. The published total syntheses of reveromycin A (1) and the assigned structure for spirofungin B (26) are described. The approach to 1 utilized a hetero-Diels-Alder reaction to construct the spiroketal fragment in a kinetic stereocontrolled manner. The synthesis of the proposed spirofungin B (26) spiroketal fragment utilized a thermodynamically controlled cyclization of a protected dihydroxyketone precursor. This allowed for the reassignment of the structure of spirofungin B as epi-spirofungin A (48).

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“…JuliaϪLythgoe coupling with the aldehyde 23 [12] furnished the hydroxysulfone 24 (95%). Direct reduction with sodium amalgam afforded the alkene 25 (74%) as a 15:1 E/ Z mixture.…”

Section: Ter(13-dioxan-4-yl)mentioning

confidence: 99%

Conformational Analysis of oligo-1,3-Dioxan-4-yls

Brandl

Hoffmann

2002

Eur. J. Org. Chem.

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Whereas simple 4,4Ј-bi(1,3-dioxanyl)s 16 and 19 displayed little conformational preference at the inter-ring bond, their derivatives 4 and 13, with equatorial methyl groups in the 5-and 5Ј-positions, each showed a strong conformational preference to populate a conformation with a gauche arrangement of the oxygen atoms. These results form the basis of a To relate material properties or biological functions of a flexible compound to structure Ϫ that is, to constitution Ϫ an understanding of the number and nature of low-energy conformations available to such a molecule is essential. In this context, we are interested in learning what modification of flexible alkane chains gives them the property that they populate predominantly one single conformation, or put another way, that they adopt a distinct shape despite maintaining flexibility. The key is to destabilize all the undesired backbone conformations related to the one desired conformation by suitable placement of substituents. A conceivable starting point for such an undertaking is represented by alkane chains bearing a single substituent at each of their secondary carbon atoms, such as 2,3,4,5-tetramethylhexane. We reported recently on the conformational analysis of meso-2,3,4,5-tetramethylhexane and of some of its derivatives. [2] The , isomer 1 should posess a distinctly different conformational behaviour. We elaborate here on how compounds with strong conformational preferences may be attained by structural modification of ,-2,3,4,5-tetramethylhexane.[ ‡] Flexible Molecules with Defined Shape, XIX. Part XVIII:Ref.[1] [a]

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Total Synthesis of Swinholide A, Preswinholide A, and Hemiswinholide A

Cited by 112 publications

References 82 publications

The First Total Synthesis of Topsentolide B₃

The First Total Synthesis of Topsentolide B₃

Total synthesis of spiroketal containing natural products: kinetic vs. thermodynamic approaches

Conformational Analysis of oligo-1,3-Dioxan-4-yls

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Total Synthesis of Swinholide A, Preswinholide A, and Hemiswinholide A

Cited by 112 publications

References 82 publications

The First Total Synthesis of Topsentolide B3

The First Total Synthesis of Topsentolide B3

Total synthesis of spiroketal containing natural products: kinetic vs. thermodynamic approaches

Conformational Analysis of oligo-1,3-Dioxan-4-yls

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The First Total Synthesis of Topsentolide B₃

The First Total Synthesis of Topsentolide B₃