First total syntheses of bicyclic marine sesquiterpenoids drechslerines A and B

Hagiwara, Hisahiro; Fukushima, Masakazu; Kinugawa, Kimihiko; Matsui, Takuya; Hoshi, Takashi; Suzuki, Toshio

doi:10.1016/j.tet.2011.04.007

Cited by 14 publications

(9 citation statements)

References 34 publications

(11 reference statements)

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“…303 Total syntheses of the bicyclic sesquiterpenoids drechslerine A and B, from culture of the algicolous fungus Drechslera dematioidea (red alga Liagora viscida), 304 were completed from (S)-carvone, utilising three palladium-catalysed reactions. 305,306 Synthesis and NMR spectroscopic analysis were used to reassign the structure and determine the absolute conguration of pericosine D 0 , a metabolite of the sea hare-derived fungus Periconia byssoides, 307 as methyl (3R,4S,5S,6S)-6-chloro-3,4,5-trihydroxy-1-cyclohexene-1-carboxylate 403. 308 Synthesis of the proposed structure of phomopsin B, 309 a metabolite of the mangrove endophytic fungus Phomopsis sp., led to revision of the structure to that of the known dothiorelone A, previously isolated from another mangrove endophytic fungus Dothiorella sp.…”

Section: Synthetic Aspectsmentioning

confidence: 99%

Marine natural products

et al. 2013

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This review covers the literature published in 2011 for marine natural products, with 870 citations (558 for the period January to December 2011) referring to compounds isolated from marine microorganisms and phytoplankton, green, brown and red algae, sponges, cnidarians, bryozoans, molluscs, tunicates, echinoderms, mangroves and other intertidal plants and microorganisms. The emphasis is on new compounds (1152 for 2011), together with the relevant biological activities, source organisms and country of origin. Biosynthetic studies, first syntheses, and syntheses that lead to the revision of structures or stereochemistries, have been included.

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Section: Synthetic Aspectsmentioning

confidence: 99%

Marine natural products

et al. 2013

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“…[40] The asymmetric silyl enol ether allylation was also applied in the synthesis of the marine sesquiterpenoides drechslerine A and B by Stoltz et al. [41] The silyl enol ether 4 could be allylated with ligand L6a leading to an excellent diastereoselectivity. Further steps including cyclization gave access to drechslerine A and B, respectively (Scheme 24).…”

Section: Silyl Enol Ethersmentioning

confidence: 99%

The Allylic Alkylation of Ketone Enolates

Junk

Kazmaier

2020

ChemistryOpen

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The palladium‐catalyzed allylic alkylation of non‐stabilized ketone enolates was thought for a long time to be not as efficient as the analogous reactions of stabilized enolates, e. g. of malonates and β‐ketoesters. The field has experienced a rapid development during the last two decades, with a range of new, highly efficient protocols evolved. In this review, the early developments as well as current methods and applications of palladium‐catalyzed ketone enolate allylations will be discussed.

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“…The first total syntheses of the bicyclic sesquiterpenoids drechslerines A and B were reported by Hagiwara et al, 144 who utilized a palladium-catalyzed conjugate reduction and carbon monoxide insertion as one of the key steps. the edible mushroom Hericium erinaceum, and a fungus of Stereum sp., respectively.…”

Section: Scheme 39mentioning

confidence: 99%

Palladium-Mediated Total Synthesis of Bioactive Natural Products

Majumdar

Sinha

2013

Synthesis

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The search for efficient synthetic procedures for natural products, drugs, and materials with economical and ecological advantages is an important area of current interst in synthetic organic chemistry. We have made an attempt to summarize the progress made in this area since 2005. This article describes the syntheses of several natural products and drugs that employ multiple palladiumcatalyzed processes in either a sequential or a domino fashion. Palladium-Mediated Synthesis of Natural Products Containing a Sugar Moiety 4 Palladium-Mediated Synthesis of Marine Natural Products 5 Palladium-Mediated Synthesis of Amino Acids and Peptides 6 Palladium-Mediated Synthesis of Terpenoids 7 Miscellaneous Natural Products 8 Conclusion

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First total syntheses of bicyclic marine sesquiterpenoids drechslerines A and B

Cited by 14 publications

References 34 publications

Marine natural products

Marine natural products

The Allylic Alkylation of Ketone Enolates

Palladium-Mediated Total Synthesis of Bioactive Natural Products

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