Both enantiomers of 12-methyl-13-tridecanolide{(R)-(+)-1 (S)-(-)-1} and 14-methyl-15-pentadecanolide (muscolide) {(R)-(+)-2 (S)-(-)-2} were synthesized from either (S)-(+)- or (R)-(-)-3-bromo-2-methyl-1-propanol 8 as a chiral building block.
TaskinenJ. (1975) 12-Methyl-omega-tridecanolide, A new macrocyclic lactone from Angelica root oil. Acta Chimica Scandinavica, Series B, 29, 637–638;
2.
TaskinenJ, NykaenenL., (1975) Chemical composition of Angelica root oil. Acta Chimica Scandinavica, Series B, 29, 757–764.
3.
VossG, GerlachH., (1983) Ortho esters with 2,4,10-trioxaadamantane structure as carboxyl protecting group; Applications in the synthesis of substituted carboxylic acids by means of Grignard reagents. Helvetica Chimica Acta, 66, 2294–2307;
KraftP, TochtermannW., (1994) Synthesis of medium and large ring compouds, XXXVIII. Ring enlargement of cyclodecanone by a chiral building block: Synthesis and olfactory properties of (12R)-(+)-12-methyl-13-tridecanolide. Liebigs Annalen der Chemie, 1161–1164;
6.
KraftP, TochtermannW., (1995) Synthesis of medium and large ring compouds, XXXIX. Stereoselective synthesis of both enantiomers of 13-tetradecanolide by ring enlargement with different chiral building brocks and olfactory comparison with (12R)-(+)- and (12S)-(-)-12-methyl-13-tridecanolide. Liebigs Annalen, 1409–1414.
7.
FürstnerA, LangemannK., (1996) Conformationally unbiased macrocyclization reactions by ring closing metathesis. Journal of Organic Chemistry, 61, 3942–3943.
8.
SchultzK, KraftP., (1997) Characterization of the macrolide fraction of Angelica root oil and enantiomeric composition of 12-methyl-13-tridecanolide. Journal of Essential Oil Research, 9, 509–514.
9.
BeckerJ, OhloffG., (1971) Eine neuartige fragmentierung bicyclisher enolaether verfaren zur darstellung macrocyclisher lactone. Helvetica Chimica Acta, 54, 2889–2895.
10.
ZalharkinLI, PryanishnikovAP, GusevaVV. (1979) Synthesis of 15-pentadecanolide and 14-methyl-15-pentadecanolide from cyclododecanoneZhurnal Organisheskoi Khmii, 15, 1441–1447.
11.
BollbuckB, KraftP, TochtermannW., (1996) Nature-like odorants by stereoselective ring enlargement of cyclohexanone and cyclododecanone. Tetrahedron, 52, 4581–4592.
12.
LopesD, StroblH, KolodziejczykP., (2004) 14-Methylpentadecano-15-lactone (muscolide): A new macrocyclic lactone from the oil of Angelica archangelica L. Chemistry and Biodiversity, 1, 1880–1887.
13.
ScafatoP, LaroccaA, RosiniC., (2006) An alternative stereoselective synthesis of the macrocyclic fragrances (R)-12-methyltridecanolide and (S)-muscolide by means of an asymmetric catalytic conjugate addition/Baeyer-Villiger oxidation. Tetrahedron: Asymmetry, 17, 2511–2515.
14.
NodaY, KashinH., (1998) Synthesis of both enantiomers of four different macrocyclic lactones. Heterocycles, 48, 5–10.
15.
KuriharaT, NakajimaY, MitsunobuO., (1976) Synthesis of lactones and cycloalkanes. Cyclization of ω-hydroxy acids and ethyl α-cyano-to-hydroxycarboxylates. Tetrahedron Letters, 17, 2455–2458.
