STEREOSPECIFIC SYNTHESIS OF (±)-Β-Santalol

Abstract

A stereospecific synthesis of 1-acetoxy-5-bromo-2-methyl-2-cis-pentene in 4 steps starting from 3-formyl-5,6-dihydro-2H-pyran, dimer of acrolein, followed by alkylation of 2-ethoxycarbonyl-3-methylbicyclo[2.2.1]hept-2-ene with the bromide furnished a facile synthesis of (±)-β-santalol.

Performance evaluation of a versatile multidimensional chromatographic preparative system based on three-dimensional gas chromatography and liquid chromatography–two-dimensional gas chromatography for the collection of volatile constituents

“…Although several synthetic procedures have been exploited for the production of such components, these ways are not cost-effective and, hence, sandalwood essential oil remains the only viable source of these sesquiterpene alcohols [11][12][13][14][15][16]. The widespread used fractional distillation may be unrewarding procedure, since these components have the tendency to be distilled at the same temperature as a mixture [17].…”

The Synthesis of Fragrant Natural Products from Santalum album L.: (+)-(Z)-?-Santalol and (–)-(Z)-?-Santalol

“…In 1981, Honda reported the highly selective exo alkylation of the enolate derived from unsaturated ester 49, in turn readily synthesized via Diels-Alder reaction, which gave the allylic acetate 50 (Scheme 25). [47] The entire side chain was installed via bromide 51 in one step with the correct alkene geometry. However, several reduction and activation steps were then needed to convert the ester group to the required methyl group.…”

Ruthenium-Catalyzed [2 + 2] versus Homo Diels–Alder [2 + 2 + 2] Cycloadditions of Norbornadiene and Disubstituted Alkynes: A DFT Study

“…Fused bicyclo­[2.2.1]­alkenes constitute a diverse class of chemical compounds and are powerful synthetic intermediates for the formation of complex, highly substituted ring systems. − Among these, bicyclo[2.2.1]­hepta-2,5-diene, colloquially known as norbornadiene 1 (NBD), has been used as a key intermediate in the total synthesis of natural products such as prostaglandin endoperoxides PGH 2 and PGG 2 , cis -Trikentrin B, and β-santalol . Photochemical isomerization between NBD derivatives and quadricyclanes is of interest as a potential photoswitchable molecule that can undergo closed cycles of solar light harvesting and energy storage and release. − Because of the rigid bicyclic structure of NBD, there is significant ring strain energy in this molecule .…”