Synthesis of methyl α-l-callipeltoside

Smith, Garry R.; Finley, J.J.; Giuliano, Robert M.

doi:10.1016/s0008-6215(98)00086-x

Cited by 27 publications

(21 citation statements)

References 8 publications

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“…As shown in Scheme 114, callipeltoside A was assembled from the aglycon 738 by a Sonogashira coupling using the alkyne 739 followed by glycosylation at C5 using the trichloroacetimidate 740, prepared from L-rhamnose (741) according to the Giuliano procedure. 65 Three strategic aldol bond disconnections at C4-C5, C8-C9, and C12-C13 of the aglycon 738 revealed the four coupling segments 742, 743, 744, and 745.…”

Section: Paterson Synthesis Of Callipeltoside a 64mentioning

confidence: 99%

Advances in the Total Synthesis of Biologically Important Marine Macrolides

2005

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Section: Paterson Synthesis Of Callipeltoside a 64mentioning

confidence: 99%

Advances in the Total Synthesis of Biologically Important Marine Macrolides

2005

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“…elected to target the L‐configured callipeltose sugar side chain (Scheme 6b). Starting from known intermediate 7 , [36] which was prepared from L‐rhamnose in nine steps, N ‐silylation followed by O ‐methylation led to 8 . Hydrolysis of the anomeric center followed by activation of the resulting hydroxyl then provided the glycosyl donor 9 .…”

Section: (−)‐Callipeltoside Amentioning

confidence: 99%

Total Synthesis in the Trost Laboratories: Selected Milestones From the Past Twenty Years

Mata¹,

Kalnmals

2021

Israel Journal of Chemistry

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Since the early days of his independent career, Prof. Barry M. Trost has maintained a keen interest in complex molecule synthesis. Over the past 55 years, Trost and coworkers have reported syntheses of more than 260 natural products, pharmaceuticals, and other complex biomolecules – a truly extraordinary feat and an incredible testament to Prof. Trost's inventiveness and ingenuity. Even more remarkably, Trost generated more than half of this output – as well as some of his most daring and ambitious syntheses – in just the past twenty years. This review provides a brief summary of all total syntheses from the Trost laboratories since 2000, as well as more detailed vignettes of sixteen particularly notable campaigns, including conquests of callipeltoside A, galanthamine and three related alkaloids, agelastatin A, terpestacin, pseudolaric acid B, ushikolide A, bryostatin 16, laulimalide, aeruginosin 98B, lasonolide A, perophoramidine, leustroducsin B, des‐epoxy‐amphidinolide N, bulleyanaline and three related alkaloids, and bryostatin 3.

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“…The callipeltoside A aglycon 97 was then obtained by concurrent acid-mediated desilylation and methylacetal hydrolysis. Finally, a Schmidt-type α-glycosylation [48] of the activated sugar 89 (accessed from L-rhamnose by modification of a known pathway) [49] with 97 followed by desilylation delivered callipeltoside A. [45] Aurisides A (105) and B (106) were isolated by the Yamada group from the sea hare Dolabella auricularia.…”

Section: Scheme 14: Structure and Retrosynthetic Analysis Of Callipelmentioning

confidence: 99%

The Stereocontrolled Total Synthesis of Polyketide Natural Products: A Thirty-Year Journey

Stockdale

Lam

Anketell

et al. 2020

Bulletin of the Chemical Society of Japan

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The diverse and complex structures of polyketide natural products have stimulated the imagination of synthetic chemists for decades. Captivated by their often impressive biological activities and their dazzling array of stereochemically-rich motifs, we have been motivated to achieve their efficient and stereocontrolled total synthesis. This review captures snapshots from our thirty-year foray into the total synthesis of 18 polyketide natural products, detailing the unique challenges, discoveries and revelations made en route to eventual success. Notably, crucial to each of these campaigns was the judicious application of highly selective aldol reactions to iteratively configure the densely oxygenated stereoclusters that characterise this fascinating class of bioactive natural products.

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Synthesis of methyl α-l-callipeltoside

Cited by 27 publications

References 8 publications

Advances in the Total Synthesis of Biologically Important Marine Macrolides

Advances in the Total Synthesis of Biologically Important Marine Macrolides

Total Synthesis in the Trost Laboratories: Selected Milestones From the Past Twenty Years

The Stereocontrolled Total Synthesis of Polyketide Natural Products: A Thirty-Year Journey

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