TY - JOUR
T1 - Contribution to the chemistry of β-pipitzol
AU - Joseph-Nathan, P.
AU - GonzáLez, M. P.
AU - Flores-Vela, A.
AU - Santillan, R. L.
AU - Román, L. U.
AU - HernáNdez, J. D.
PY - 1985/7
Y1 - 1985/7
N2 - Exploration of the chemistry of β-pipitzol (1a) leads to the preparation of a series of new derivatives, thus allowing its correlation with ent-3-epi-a-cedrene (18) known as 3-epi-α-cedrene. Alcohol 2, obtained by LiAlH4reduction of O-methyl-β-pipitzol (1c), undergoes 1–4 dehydration on acid treatment, giving the ketoalcohol 3, which differs only in the stereochemistry at C-9 from the ketoalcohol 4a obtained by Li/NH3 reduction of lc, followed by acid treatment. Moreover, hydrolysis of 4-desoxo-β-pipitzol benzoate (12) and of 4, 9-bis-desoxo-β-pipitzol benzoate (15) yields ketones 10 and 16, respectively, which differ in the stereochemistry of the methyl group at C-6. Catalytic hydrogenation of ketoalcohol 3 followed by oxidation gave the diketone 9, which is epimeric at C-6 with the diketone 10, its stereochemistry being deduced from ord measurements. Spectroscopic data and stereochemical assignment for all compounds are provided.
AB - Exploration of the chemistry of β-pipitzol (1a) leads to the preparation of a series of new derivatives, thus allowing its correlation with ent-3-epi-a-cedrene (18) known as 3-epi-α-cedrene. Alcohol 2, obtained by LiAlH4reduction of O-methyl-β-pipitzol (1c), undergoes 1–4 dehydration on acid treatment, giving the ketoalcohol 3, which differs only in the stereochemistry at C-9 from the ketoalcohol 4a obtained by Li/NH3 reduction of lc, followed by acid treatment. Moreover, hydrolysis of 4-desoxo-β-pipitzol benzoate (12) and of 4, 9-bis-desoxo-β-pipitzol benzoate (15) yields ketones 10 and 16, respectively, which differ in the stereochemistry of the methyl group at C-6. Catalytic hydrogenation of ketoalcohol 3 followed by oxidation gave the diketone 9, which is epimeric at C-6 with the diketone 10, its stereochemistry being deduced from ord measurements. Spectroscopic data and stereochemical assignment for all compounds are provided.
UR - http://www.scopus.com/inward/record.url?scp=9144227864&partnerID=8YFLogxK
U2 - 10.1021/np50040a011
DO - 10.1021/np50040a011
M3 - Artículo
AN - SCOPUS:9144227864
SN - 0163-3864
VL - 48
SP - 585
EP - 591
JO - Journal of Natural Products
JF - Journal of Natural Products
IS - 4
ER -