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Chem.. 1975, 40, 264. 217 2Ix 30 Terpenoids and Steroids Selenium dioxide oxidation of isopulegol acetate (133; 3R) and neoisopulegol acetate (133; 3 s ) is allylic oxidation is consistent with the Sharpless mechanism but a different mechanism is proposed. Voi. 4, p. 226 (135) (136) ( 1 37) Cyclic hydroboration of ( +)-limonene with thexylborane yields the pure borabicyclic compound ( 138), which is oxidized to the diol(32; X = OH) or protonolysed with acetic acid to yield pure (-)-carvomenthol (32; X = H ) after the usual ~ x i d a t i o n .
R . Bekker, M. G. Romanyuk, T. M. Filippova, N. I. Zakharova, and C. I. Sarnokhvalov,J. Org. Chem. ),1974, 10,1873. T. Kishimoto and Y. Matsubara, Nippon Nagaku Kaishi, 1975, 701. B. Corbier and P. Teisseire, Recherches, lY74, 19, 253. H. R. Ansari and R. Clark, Tetrahedron Letters, 1975, 3085. 19 Monoterpenoids Reagents: i, HNO,; ii, LiAlH,; iii, p-TsCl-py; iv, aq. KOH; v, diethyl malonate-NaOEt; vi, aq. KOH; vii, aq. H,SO,; viii, CH,O-Et,NH; ix, PhSeH; x, BulAlH-THF; xi, Ph,P( Me)Br-NaH-DMSO.
Trost and D. E. Keeley, J. Org. , 1975,40, 2013. 22 Terpenoids and Steroids synthesized conventionally from the corresponding ci~-bicyclo[3,2,0]heptanone, yields the keto-acid (76),'63 which has previously been converted into grandisol(73). (73) (74) (75) (76) A second synthesis of chiral grandisol (73) from trans-pinan-2P-01 (77; X = H) derived from (-)-P-pinene, as shown in Scheme 8, involves the useful photochemical $-t 4 l-lll,+b (77) (73) t o 4-5 V-Vll,I'-. && p H c . ~ ~ . - ~ o A c ~ ~ H ' T (79) H (78) Reagents: i , Nitrite ester, hv; ii, A ; iii, ether-acetone-2% aq.