OPTICALLY PURE DIHYDROXY GAMMA-ALKYLATED GAMMA-BUTYROLACTONES STARTING FROM L-TARTARIC ACID - APPLICATION TO FORMAL AND TOTAL SYNTHESES OF NATURAL-PRODUCTS
Am. Fernandez et al., OPTICALLY PURE DIHYDROXY GAMMA-ALKYLATED GAMMA-BUTYROLACTONES STARTING FROM L-TARTARIC ACID - APPLICATION TO FORMAL AND TOTAL SYNTHESES OF NATURAL-PRODUCTS, Journal of organic chemistry, 62(12), 1997, pp. 4007-4014
A general and efficient preparation of epimeric optically pure gamma-b
utyrolactones 2 and 3 is described starting from L-tartaric acid (1).
These lactones are well-known to be important building blocks in the s
yntheses of natural products. L-Tartaric acid (1) was transformed into
carbonylated chirons (ketones 4 and aldehyde 5). These chirons, when
submitted to highly stereoselective reactions (reduction or organometa
llic addition), led to epimeric dihydroxy gamma-butyrolactones 2 and 3
after lactonization and deprotection steps. The resulting optically p
ure lactones are precursors of biological compounds and have allowed a
total synthesis of L-biopterin and formal syntheses of quercus lacton
e, dodecanolactone, avenaciolide, and tetrahydrocerulenin.