Convergent synthesis of the ABCDE-ring part of ciguatoxin CTX3C

Fujiwara, Kenshu; Goto, Akiyoshi; Sato, Daisuke; Ohtaniuchi, Yuko; Tanaka, Hideki; Murai, Akio; Kawai, Hidetoshi; Suzuki, Takanori

doi:10.1016/j.tetlet.2004.07.145

Cited by 40 publications

(3 citation statements)

References 37 publications

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“…The benzylidene acetal of 7 was removed and the primary alcohol was selectively protected with TBDPS to afford 8 in a 69% yield in two steps. The glycosyl acceptor (8) was coupled with 2,3,4,6-tetra-O-acetyl-α-D-galactopyranosyl trichloroacetimidate (9) in the presence of TMSOTf at −20°C. However, desired disaccharide 10 could only be obtained in a 2% yield under these reaction conditions.…”

Section: Resultsmentioning

confidence: 99%

Synthesis of biotinylated keratan sulfate repeating disaccharides

Takeda

Tamura

2014

Bioscience, Biotechnology, and Biochemistry

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Section: Resultsmentioning

confidence: 99%

Synthesis of biotinylated keratan sulfate repeating disaccharides

Takeda

Tamura

2014

Bioscience, Biotechnology, and Biochemistry

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“…The synthesis of the ABCDE-ring fragment of ciguatoxin CTX3C ( 4 ) was achieved by means of the above methodology (Scheme ) . Deprotonation of AB-ring segment 218 with NaHMDS followed by reaction with E-ring aldehyde 219 gave the adduct, which was transformed to α-hydroxy ketone 220 in two steps.…”

Section: 7 Dithioacetal S-oxide Coupling/stepwise Reductive Etherific...mentioning

confidence: 99%

“…Acidic removal of the TBS and methylthio methylsulfinyl acetal groups of 214, followed by Lewis-acid-mediated hydroxyketone The synthesis of the ABCDE-ring fragment of ciguatoxin CTX3C (4) was achieved by means of the above methodology (Scheme 27). 85…”

Section: Dithioacetal S-oxide Coupling/stepwise Reductive Etherificationmentioning

confidence: 99%

Convergent Strategies for Syntheses of trans-Fused Polycyclic Ethers

Inoue

2005

Chem. Rev.

212

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Allylboration of Carbonyl Compounds

Lachance

Hall

2009

Organic Reactions

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Allylic boron compounds have gained a prominent status in organic synthesis for their ability to add with high stereoselectivity to carbonyl compounds such as aldehydes, making them a methodology of choice for the preparation of acetate and propionate units found in several classes of natural products. This remarkable reaction process was discovered in 1964, only to become popular in the 1980s. Using either the dialkylborane or boronate reagents, both the thermal uncatalyzed reaction and the more recent acid‐catalyzed procedures can provide homoallylic alcohol products in high enantioselectivity. The wide of range of possibilities for substitution on the reagent's allylic unit has led to the development of numerous reagents, and the residual alkene unit in the products confers to allylboration chemistry a unique versatility. This chapter presents an exhaustive survey of the useful reagents and their associated carbonyl substrates employed in organic synthesis. The mechanisms and parameters of the reaction are discussed, along with an overview of the different preparative methods for allylic boron reagents. The scope and limitations of these reagents in enantioselective additions, doubly diastereoselective additions, tandem reactions, and other variants is emphasized in the context of applications in natural product synthesis. The literature is covered through early 2006.

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Convergent synthesis of the ABCDE-ring part of ciguatoxin CTX3C

Cited by 40 publications

References 37 publications

Synthesis of biotinylated keratan sulfate repeating disaccharides

Synthesis of biotinylated keratan sulfate repeating disaccharides

Convergent Strategies for Syntheses of trans-Fused Polycyclic Ethers

Allylboration of Carbonyl Compounds

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