Palladium catalyzed stereospecific cyclization of hydroxy epoxides. Stereocontrolled synthesis of cis- and trans-2-alkenyl-3-hydroxytetrahydropyrans

Suzuki, Toshio; Sato, Ohki; Hirama, Masahiro

doi:10.1016/s0040-4039(00)97722-0

Cited by 86 publications

(31 citation statements)

References 17 publications

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“…[a] Laboratoire de Synthèse Asymétrique, associé au CNRS, UMR 5181, CPE Lyon, Université Pd 0 -catalyzed intramolecular heteroannulation through allylic alkylation, the so-called Tsuji-Trost reaction, generally employs allylic acetates, [7][8][9][10][11] benzoates, [12] carbonates, [13][14][15][16] or vinyl epoxides [8,17,18] bearing a hydroxy group. Allylsilanes have also been used as precursors of the η 3 -allyl intermediates, starting from PdCl 2 and CuCl 2 , affording the corresponding THF derivatives in quite good yields.…”

Section: Introductionmentioning

confidence: 99%

Palladium‐Catalyzed Formation of Cyclic Ethers – Regio‐, Stereo‐ and Enantioselectivity of the Reaction

2007

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An efficient and stereoselective synthesis of 3‐alkyl‐3‐hydroxymethyl‐5‐vinyltetrahydrofurans is described by the Pd0‐catalyzed cyclization of the methyl carbonates of ω,ω‐bis(hydroxymethyl)‐α,β‐unsaturated alcohols. The use of chiral ligands gave the corresponding THF derivatives in low to moderate enantiomeric ratios. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2007)

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Section: Introductionmentioning

confidence: 99%

Palladium‐Catalyzed Formation of Cyclic Ethers – Regio‐, Stereo‐ and Enantioselectivity of the Reaction

2007

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“…Early on, we developed enantioselective routes to the medium (7-, 8-, and 9-membered) ring ethers of ciguatoxins 27–31) and the circular dichroism (CD) studies of synthetic AB ring fragments implicated the absolute configuration of CTXs. 28,32,33) Then, we quickly realized that convergent assembly of the structural fragments was the key for successful construction of the huge ladder-like polycyclic ether system.…”

Section: Determination Of the Absolute Configuration Of Ciguatoxins Amentioning

confidence: 99%

Total synthesis and related studies of large, strained, and bioactive natural products

Hirama

2016

Proceedings of the Japan Academy. Ser. B: Physical and Biologic

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Our chemical syntheses and related scientific investigations of natural products with complex architectures and powerful biological activities are described, focusing on the very large 3 nm-long polycyclic ethers called the ciguatoxins, highly strained and labile chromoprotein antitumor antibiotics featuring nine-membered enediyne cores, and extremely potent anthelmintic macrolides called the avermectins.

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“…Ethers are one of the most fundamental structures of natural products [1][2][3] and carbohydrates 4) ; thus, the development of general, straightforward synthetic methods for their preparation has received much attention. Methods whereby only H 2 O is produced as a byproduct, such as dehydrative etherification, are desirable yet challenging synthetic process.…”

Section: Regular Articlementioning

confidence: 99%

Lewis Acid-Catalyzed Propargylic Etherification and Sulfanylation from Alcohols in MeNO2-H2O

Ohta

Koketsu

Nagase

et al. 2011

CHEMICAL & PHARMACEUTICAL BULLETIN

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Results of screening of other etherification conditions using 1a are shown in Table 1. Various metals, mainly lanthanoids, were found to be effective for etherifications in MeNO 2 -H 2 O. Next, we selected propargyl alcohols bearing other aromatic substituents as starting materials and performed etherifications under the suitable condition using Sc(OTf) 3 /MeNO 2 -H 2 O at 30°C. With the Sn(OTf) 2 system, the product 2aa was also obtained in the satisfactory yield, however, a small amount of unknown compounds were contaminated. Results of these comparisons are shown in Table 1.Using the same substrate, 3-p-methoxyphenylpropargyl alcohol 1a, etherification with 1°alcohols including methanol, dodecanol and geraniol as nucleophiles produced products 2ab, 2ac and 2af, respectively, in good yields (entries 1, 2

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Palladium catalyzed stereospecific cyclization of hydroxy epoxides. Stereocontrolled synthesis of cis- and trans-2-alkenyl-3-hydroxytetrahydropyrans

Cited by 86 publications

References 17 publications

Palladium‐Catalyzed Formation of Cyclic Ethers – Regio‐, Stereo‐ and Enantioselectivity of the Reaction

Palladium‐Catalyzed Formation of Cyclic Ethers – Regio‐, Stereo‐ and Enantioselectivity of the Reaction

Total synthesis and related studies of large, strained, and bioactive natural products

Lewis Acid-Catalyzed Propargylic Etherification and Sulfanylation from Alcohols in MeNO2-H2O

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