Publication

Synthesis of a C29-C51 Subunit of Spongistatin 1 (Altohyrtin A) Starting from (R)-3-Benzyloxy-2-methylpropan-1-ol

Pierre Vogel
2000
Journal Articles

Abstract

A protected C29-C51 subunit ((+)-38) of Spongistatin 1 has been obtained. Key steps involve the aldol condensation of (3S,4R)-3-methyl-7-[(paramethoxybenzyl)oxy]-4-[(triethylsilyl)oxy]octan-2-one ((-)-6) with (tert-butyl)dimethylsilyl 4-deoxy-2,3-di-O-(methoxymethyl)-4-methyl-6-O-(tert-butyl)dimethylsilyl)--D-glycero-L-gluco-heptodialdo-1,5-pyranoside ((+)-7), and a C-glycosidation of (4R,7R&S,E)-7,8-dichloro-2-methylidene-1-(trimethylsilyl)oct-5-en-4-yl paramethoxybenzoate (16). Aldehyde (+)-7 was derived from (R)-3-benzyloxy-2-methylpropan-1-ol ((+)-10) in 13 formal steps but requiring the isolation of 5 intermediate products only. The longest linear synthetic scheme converts (+)-10 into (+)-38 in 2% overall yield (isolation of 11 intermediate products).

Official source

https://infoscience.epfl.ch/entities/publication/b18fa3cc-eb6e-4bc9-9d95-9096746dedd8

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Pierre Vogel
2000
Journal Articles

Abstract

Official source

https://infoscience.epfl.ch/entities/publication/b18fa3cc-eb6e-4bc9-9d95-9096746dedd8

About this result

Related concepts (8)

Glycoside

In chemistry, a glycoside ˈɡlaɪkəsaɪd is a molecule in which a sugar is bound to another functional group via a glycosidic bond. Glycosides play numerous important roles in living organisms. Many plants store chemicals in the form of inactive glycosides. These can be activated by enzyme hydrolysis, which causes the sugar part to be broken off, making the chemical available for use. Many such plant glycosides are used as medications. Several species of Heliconius butterfly are capable of incorporating these plant compounds as a form of chemical defense against predators.

Glycosidic bond

A glycosidic bond or glycosidic linkage is a type of ether bond that joins a carbohydrate (sugar) molecule to another group, which may or may not be another carbohydrate. A glycosidic bond is formed between the hemiacetal or hemiketal group of a saccharide (or a molecule derived from a saccharide) and the hydroxyl group of some compound such as an alcohol. A substance containing a glycosidic bond is a glycoside.

Aldol reaction

The aldol reaction (aldol addition) is a reaction that combines two carbonyl compounds (aldehydes or ketones) to form a new β-hydroxy carbonyl compound. These products are known as aldols, from the aldehyde + alcohol, a structural motif seen in many of the products. The use of aldehyde in the name comes from its discovery history, where aldehydes were first used in the reaction and not ketones. Aldol structural units are found in many important molecules, whether naturally occurring or synthetic.